Journal Article
References for Ch242 (2005)
References for 11/28/05
- 12/02/05
1a.
Total synthesis of (.+-.)-methyl homosecodaphniphyllate.
A remarkable new tetracyclization reaction
Roger B. Ruggeri, Marvin M. Hansen, Clayton H. Heathcock;
J.
Am. Chem. Soc.; 1988; 110(26); 8734-8736
1b. The Enchanting Alkaloids of Yuzuriha.
Heathcock, Clayton H.;
Angew. Chem., Int. Ed. Engl., 1992, 31(6), 665-681.
MIL-8 Ch 242 Reserve
2.
Catalytic Asymmetric Diels-Alder Reactions.
Yujiro Hayashi
in: Cycloaddition reactions in organic synthesis /
edited by Shu Kobayashi and Karl Anker Jorgensen.
Wiley-VCH, 2002. Pages 1-55.
MIL-8
Ch 242 Reserve
---------------------------------
RESERPINE
1a. Total synthesis of reserpine.
Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W.
Tetrahedron (1958), 2 1-57.
MIL-8 Reserve Ch242
1b.
Reserpine
Woodward,
R.B.
in Classics in total synthesis : targets, strategies, methods.
Nicolaou, K.C. and E.J. Sorensen ; with a foreword by E.J. Corey
Chapt. 4, pp. 55-64. VCH, c1996
MIL-8 Reserve Ch242
MIL-1 Reserve QD262 N52 1996
ESTRONE
1a. Estrone
Vollhardt,
K.P.C.
in Classics in total synthesis : targets, strategies, methods.
Nicolaou, K.C. and E.J. Sorensen ; with a foreword by E.J. Corey
Chapt. 10, pp. 153-161. VCH, c1996
MIL-8 Reserve Ch242
MIL-1 Reserve QD262 N52 1996
1b. Transition-metal-catalyzed alkyne cyclizations.
A cobalt-mediated total synthesis of dl-estrone
Raymond L. Funk, K. Peter C. Vollhardt;
J.
Am. Chem. Soc.; 1980; 102(16); 5253-5261
1c. Cobalt-mediated [2+2+2]-cycloadditions:
a maturing synthetic strategy.
Vollhardt, K. Peter C..
Angew. Chem. Int. Ed. Engl.; (1984); 23(8); 539-556.
MIL-8 Reserve Ch242
1d. Transition-metal-catalyzed acetylene cyclizations in organic synthesis
K. Peter C. Vollhardt;
Acc.
Chem. Res.; 1977; 10(1); 1-8
1e. Metal-Catalyzed Cyclooligomerization of Alkynes
Louis
S. Hegedus
in
Transition metals in the synthesis of complex organic molecules
2nd ed., pp. 234-235. University
Science Books, c1999
MIL-8 Reserve Ch242
MIL-1 Reserve QD411 H45 1999
PROSTAGLANDIN F2[alpha]
1a. Prostaglandin F2[alpha] PGF2[alpha] and Prostaglandin E2 (PGE2)
Corey,
E.J.
in Classics in total synthesis : targets, strategies, methods.
Nicolaou, K.C. and E.J. Sorensen ; with a foreword by E.J. Corey
Chapt. 5, pp. 65-82. VCH, c1996
MIL-8 Reserve Ch242
MIL-1 Reserve QD262 N52 1996
1b. Prostaglandin synthesis.
Jasjit S. Bindra, Ranjna Bindra
Academic Press, 1977
MIL-9 QP801 P68 B56
2a. Stereo-controlled synthesis of dl-prostaglandins F2.alpha. and E2
Elias J. Corey, Ned M. Weinshenker, Thomas K. Schaaf, Willy Huber;
J.
Am. Chem. Soc.; 1969; 91(20); 5675-5677
2b. Total synthesis of prostaglandins F2a and E2 as the naturally occurring
forms.
Corey,
Elias J.; … Weinshenker, Ned M.
J.
Amer. Chem. Soc. (1970), 92 397-8
2c. Total synthesis of prostaglandins F1.alpha., E1, F2.alpha.,
and
E2 (natural forms) from a common synthetic intermediate
Elias J. Corey, Ryozi Noyori, Thomas K. Schaaf;
J.
Am. Chem. Soc.; 1970; 92(8); 2586-2587
2d. Ketene equivalents.
Ranganathan, S.; Ranganathan, D.; Mehrotra, A. K.
Synthesis (1977), (5), 289-96
3. Preparation of an optically active prostaglandin intermediate via asymmetric
induction
E. J. Corey, Harry E. Ensley;
J.
Am. Chem. Soc.; 1975; 97(23); 6908-6909
4a. Practical enantioselective Diels-Alder and aldol reactions using a new
chiral controller system
E. J. Corey, Rene Imwinkelried, Stanislaw Pikul, Yi Bin Xiang;
J.
Am. Chem. Soc.; 1989; 111(14); 5493-5495
4b. Catalytic enantioselective synthesis of a key intermediate for the
synthesis of prostanoids.
Corey, E. J.; Imai, Nobuyuki; Pikul, Stanislaw.
Tetrahedron Letters (1991), 32(51), 7517-20.
MIL-8 Reserve Ch242
5a. First application … intramolecular interactions … design of
chiral catalysts for highly enantioselective Diels-Alder reactions
E. J. Corey, Teck Peng Loh;
J.
Am. Chem. Soc.; 1991; 113(23); 8966-8967
5b. The origin of greater than 200:1 enantioselectivity in a catalytic
Diels-Alder reaction …
E. J.
Corey, Teck Peng Loh, Thomas D. Roper, Mihai D. Azimioara, Mark C. Noe;
J.
Am. Chem. Soc.; 1992; 114(21); 8290-8292
(+)FR 182877
1a. A Synthesis of (+)-FR182877, Featuring Tandem Transannular Diels-Alder
Reactions Inspired by a Postulated Biogenesis
Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J.;
J.
Am. Chem. Soc.; 2002; 124(17); 4552-4553
Supporting
Information
1b. Intramolecular Allenolate Acylations in Studies toward a Synthesis of
FR182877
Vanderwal, C. D.; Vosburg, D. A.; Sorensen, E. J.;
Org.
Lett.; 2001; 3(26); 4307-4310
Supporting
Information
1c. A cascade cycloaddition strategy leading to the total synthesis of
(-)-FR182877.
Evans, David A.; Starr, Jeremy T.
Angew.
Chem. Int. Ed.; (2002); 41(10);
1787-1790
References for
11/23/05
1a.
ACCELERATION OF THE DIELS-ALDER REACTION BY ALUMINUM CHLORIDE
Peter Yates, Philip Eaton;
J.
Am. Chem. Soc.; 1960; 82(16); 4436-4437
1b. CATALYSIS OF THE DIELS-ALDER REACTION
G. I. Fray, R. Robinson;
J.
Am. Chem. Soc.; 1961; 83(1); 249-249
1c. SOME PREPARATIONS FROM MALEIC AND FUMARIC ACIDS
Harold G. Oddy;
J.
Am. Chem. Soc.; 1923; 45(9); 2156-2160
2. Intramolecular Cycloadditions between Cyclobutadiene and Alkenes
Tallarico, J. A.; Randall, M. L.; Snapper, M. L.;
J.
Am. Chem. Soc.; 1996; 118(38); 9196-9197
Supporting
Information
3a. Catalytic Enantioselective Diels-Alder Reactions:
Methods, Mechanistic Fundamentals, Pathways, and Applications
E. J. Corey
Angew.
Chem. Int. Ed.; 2002, 41(10), 1650-1667
3b. The Diels-Alder Reaction in Total Synthesis
K. C. Nicolaou, Scott A. Snyder, Tamsyn Montagnon, Georgios Vassilikogiannakis
Angew.
Chem. Int. Ed.; 2002, 41(10), 1668-1698
4. Preparation of an optically active prostaglandin intermediate via asymmetric
induction
E. J. Corey, Harry E. Ensley;
J.
Am. Chem. Soc.; 1975; 97(23); 6908-6909
5. Chelate-controlled carbonyl addition reactions.
The exceptional chelating ability of dimethylaluminum chloride and
methylaluminum dichloride.
Evans, David A.; Allison, Brett D.; Yang, Michael G.
Tetrahedron
Letters (1999), 40(24), 4457-4460
6a. New synthetic methods.
Intramolecular [4+2]- and [3+2]-cycloadditions in organic synthesis
Oppolzer, Wolfgang.
Angew. Chem. Int. Ed. Engl. (1977), 16(1), 10-24.
MIL-8 RESERVE Ch242
6b. The intramolecular Diels-Alder reaction
Ciganek, Engelbert.
Org. React. (NY); (1984), 32, 1-374.
MIL-8 REFERENCE QD 261 O7 v.32
7a. An intramolecular Diels-Alder route
to eudesmane sesquiterpenes
Stephen R. Wilson, David T. Mao;
J.
Am. Chem. Soc.; 1978; 100(19); 6289-6291
7b. Intramolecular Diels-Alder Reactions. III.
Cyclizations of trans-Cinnamyl and Phenylpropargyl Phenylpropiolates1a
L. H. Klemm, D. Hsu Lee, K. W. Gopinath, C. E. Klopfenstein;
J.
Org. Chem.; 1966; 31(7); 2376-2380
7c. Stereocontrol in the intramolecular Diels-Alder reaction. 1.
An application to the total synthesis of (.+-.) marasmic acid
Robert K. Boeckman , Jr., Soo Sung Ko;
J.
Am. Chem. Soc.; 1980; 102(23); 7146-7149
7d. Intramolecular Diels-Alder reactions:
the angularly methylated trans-perhydroindan ring system
William R. Roush, Steven M. Peseckis;
J.
Am. Chem. Soc.; 1981; 103(22); 6696-6704
7e. Synthesis of antibiotic SS-228R.
Strong base induced cycloaddition of homophthalic anhydrides
Yasumitsu Tamura, Fumio Fukata, Manabu Sasho, Teruhisa Tsugoshi, Yasuyuki Kita;
J.
Org. Chem.; 1985; 50(13); 2273-2277
7f. Simple regioselective synthesis of trans-7a-methylhydrind-4-en-1-one,
a key intermediate for steroid total synthesis
Jung, Michael E.; Halweg, Kim M.
Tetrahedron Letters (1981), 22(40), 3929-32.
MIL-8 Reserve Ch 242
8. Asymmetric Diels-Alder cycloaddition reactions with chiral
.alpha.,.beta.-unsaturated N-acyloxazolidinones
David A. Evans, K. T. Chapman, J. Bisaha;
J.
Am. Chem. Soc.; 1988; 110(4); 1238-1256
References for
11/21/05
1.
The thermal, aliphatic Claisen rearrangement
Frederick E. Ziegler;
Chem.
Rev.; 1988; 88(8); 1423-1452
2a. Synthetic studies on (2R,4'R,8'R)-.alpha.-tocopherol.
Facile syntheses of optically active, saturated, acyclic isoprenoids via
stereospecific [3,3] sigmatropic rearrangements
Ka-Kong Chan, Noal Cohen, James P. De Noble, Anthony C. Specian , Jr., Gabriel
Saucy;
J.
Org. Chem.; 1976; 41(22); 3497-3505
2b. A novel total synthesis of (2R,4'R,8'R)-.alpha.-tocopherol (vitamin E).
Construction of chiral chromans from an optically active, nonaromatic precursor
Noal Cohen, Rocco J. Lopresti, Gabriel Saucy;
J.
Am. Chem. Soc.; 1979; 101(22); 6710-6716
3. Enantioselective hydrogenation of allylic and homoallylic alcohols
Hidemasa Takaya ... Ryoji Noyori;
J.
Am. Chem. Soc.; 1987; 109(5); 1596-1597
4a. Asymmetric Claisen rearrangement catalyzed by chiral organoaluminum reagent
Keiji Maruoka, Hiroshi Banno, Hisashi Yamamoto;
J.
Am. Chem. Soc.; 1990; 112(21); 7791-7793
4b. Enantioselective activation of ethers by chiral organoaluminum reagents:
application to asymmetric Claisen rearrangement.
Maruoka, Keiji; Banno, Hiroshi; Yamamoto, Hisashi.
Tetrahedron: Asymmetry (1991), 2(7), 647-62.
MIL-8 Ch 242 Reserve
5. Highly enantioselective and diastereoselective Ireland-Claisen rearrangement
of achiral allylic esters
E. J. Corey, Duck Hyung Lee;
J.
Am. Chem. Soc.; 1991; 113(10); 4026-4028
6. The Catalytic Enantioselective Claisen Rearrangement of an Allyl Vinyl Ether
Lars Abraham, Regina Czerwonka, Martin Hiersemann.
Angew.
Chem. Int. Ed.; (2001); 40(24); 4700-4703
7. Discoveries Missed, Discoveries Made:
Two
Case Studies of Creativity in Chemistry.
In
Chemical Creativity
Jerome A. Berson
Chapter
2, pages 9-32.
Wiley-VCH, 1999
MIL-8 Ch 242 Reserve
Revised from: Tetrahedron (1992),
48(1), 3-17
8. Cycloaddition reactions in organic synthesis
W. Carruthers.
Pergamon Press, 1990.
Tetrahedron organic chemistry series ; v. 8.
MIL-8 Ch 242 Reserve
9a. Diels-Alder reaction with maleic anhydride.
Kloetzel, Milton C.
Org. React. (NY); (1948), 4, 1-59.
MIL-8 REFERENCE QD 251 O7
9b. Diels-Alder reaction: ethylenic and acetylenic dienophiles.
Holmes, H. L.
Org. React. (NY); (1948), 4, 60-173.
MIL-8 REFERENCE QD 251 O7
9c. Diels-Alder reaction: quinones and other cyclenones.
Butz, Lewis W.
Org. React. (NY); (1949), 5, 136-92.
MIL-8 REFERENCE QD 251 O7
9d. The intramolecular Diels-Alder reaction.
Ciganek, Engelbert.
Org. React. (NY); (1984), 32, 1-374.
MIL-8 REFERENCE QD 251 O7
10. Frontier orbitals and organic chemical reactions.
Ian Fleming.
Wiley, c1976.
MIL-8 Ch 242 Reserve
References for
11/18/05 - Synthesis Friday (K252a) - Week 8
Total
Synthesis of (+)-K252a and (-)-K252a.
Wood,
J. L., B. M. Stoltz, et al.
J.
Am. Chem. Soc.; 1995, 117(41), 10413-10414.
Total synthesis of (+)-RK-286c, (+)-MLR-52, (+)-staurosporine, and (+)-K252a.
Wood,
J. L., B. M. Stoltz, et al.
J.
Am. Chem. Soc.; 1996, 118(43), 10656-10657
Design and implementation of an efficient synthetic approach to furanosylated
indolocarbazoles:
Total synthesis of (+)- and (- )-K252a.
Wood,
J. L., B. M. Stoltz, et al.
J.
Am. Chem. Soc.; 1997, 119(41), 9641-9651
Design and implementation of an efficient synthetic approach to pyranosylated
indolocarbazoles:
Total synthesis of (+)-RK286c, (+)-MLR-52, (+)-staurosporine, and
(-)-TAN-1030a.
Wood,
J. L., B. M. Stoltz, et al.
J.
Am. Chem. Soc.; 1997, 119(41), 9652-9661
Development of a rhodium carbenoid-initiated claisen rearrangement
for the enantioselective synthesis of alpha- hydroxy carbonyl compounds.
Wood,
J. L. ... B. M. Stoltz, et al.
J.
Am. Chem. Soc.; 1999, 121(8), 1748-1749
Total
synthesis of the macrolide antibiotic cytovaricin
Evans,
D. A. … Stout, T. J.
J.
Am. Chem. Soc.; 1990, 112(19), 7001-7031
References for
11/16/05
1a. Organic chemistry
G. Marc Loudon.
4th ed., 2002.
MIL-1 Reserve
1b. Advanced organic chemistry
Frank A. Carey and Richard J.
Sundberg.
Part A. 4th ed., 2000.
MIL-1 Reserve / MIL-8 Reserve Ch 144
2. The Introduction of Substituted Vinyl Groups. V.
A Rearrangement Involving the Migration of an Allyl Group in a Three-Carbon
System.
Arthur C. Cope, Elizabeth M. Hardy.
J.
Am. Chem. Soc.; 1940; 62; 441-444
3. The overlap of two allyl radicals or a four-centered transition state in the
Cope rearrangement.
Doering, W. v. E.; Roth, W. R.
Tetrahedron (1962); 18; 67-74.
MIL-8 Reserve Ch 242
4. Isolation and characterization of cis-divinylcyclopropane.
Brown, John M.; Golding, Bernard T.; Stofko, John J., Jr.
J. Chem. Soc.,
Chem. Commun.; 1973(9); 319-20.
5a. [3,3] Sigmatropic rearrangements of 1,5-diene alkoxides.
Powerful accelerating effects of the alkoxide substituent
D. A. Evans, A. M. Golob;
J.
Am. Chem. Soc.; 1975; 97(16); 4765-4766
5b. Theoretical studies of the oxy anionic substituent effect
Michael L. Steigerwald, William A. Goddard , III, David A. Evans;
J.
Am. Chem. Soc.; 1979; 101(8); 1994-1997
6a. (+/-)-Periplanone-B.
Total synthesis and structure of the sex excitant pheromone of the American
cockroach
W. Clark Still;
J.
Am. Chem. Soc.; 1979; 101(9); 2493-2495
6b. Cyclobutene bridgehead olefin route to the American cockroach sex
pheromone, periplanone-B
Stuart L. Schreiber, Conrad Santini;
J.
Am. Chem. Soc.; 1984; 106(14); 4038-4039
7. Strychine
L. Overman.
Classics in Total Synthesis / K.C. Nicolau.
1996, Chapter 33, pp. 641-653.
MIL-1 Reserve / MIL-8 Reserve Ch 242
8. Uber umlagerung von phenol-allyl-athern in C-allyl-phenole.
Claisen, L..
Ber. Dtsch. Chem. Ges.; 1913; 45; 3157-66.
Rearrangement of Phenol Allyl Ethers into C-Allylphenols. [extended abstract]
J. Chem. Soc. Abstr.; 1912; 102(1);
965-966.
MIL-8 Reserve Ch 242
9. Claisen'sche umlagerungen bei allyl- und benzylalkoholen mit hilfe von
acetalen des N,N-diemtylacetamids.
Wick, A. E.; Felix, Dorothee; Steen, Katharina; Eschenmoser, A.
Helv. Chim. Acta; 1964; 47; 2425-9.
Claisen rearrangement of allyl and
benzyl alcohols by N,N-dimethylacetamide acetals.
Chem. Absts. 1965; 62:36963
MIL-8 Reserve Ch 242
10. Simple stereoselective version of the Claisen rearrangement leading to
trans-trisubstituted olefinic bonds.
Synthesis of squalene
William Summer Johnson, ... Michael R. Petersen;
J.
Am. Chem. Soc.; 1970; 92(3); 741-743
11. Claisen rearrangement of allyl esters
Robert E. Ireland, Richard H. Mueller;
J.
Am. Chem. Soc.; 1972; 94(16); 5897-5898
References for
11/14/05
1.
Zur Aktivierung Lithiumorganischer reagenzien.
Schlosser, Manfred.
J. Organomet. Chem.; 1967; 8(1); 9-16.
Activation
of organolithium reagents
Chem.
Absts.; 1967; 66:85806
MIL-8 Ch 242 Reserve
2. Further studies on chromium(II)-mediated homoallylic
alcohol syntheses.
Lewis, Michael D.; Kishi, Yoshito.
Tetrahedron Lett.; 1982; 23(23); 2343-6.
MIL-8 Ch 242 Reserve
3.
Diastereoselective Reactions of Chiral Allyl and Allenyl Silanes with Activated
C:X p-Bonds.
Masse, Craig E.; Panek, James S.
Chem. Rev.; 1995; 95(5); 1293-1316
References for 11/11/05 - Synthesis Friday (Monensin) - Week 7
1a. Synthesis of the polyether antibiotic monensin. 1.
Strategy and degradations
David B. Collum, John H. McDonald , III, W. Clark Still;
J. Am. Chem. Soc.; 1980; 102(6); 2117-2118
1b. Synthesis of the polyether antibiotic monensin. 2.
Preparation of intermediates
David B. Collum, John H. McDonald , III, W. Clark Still;
J. Am. Chem. Soc.; 1980; 102(6); 2118-2120
1c. Synthesis of the polyether antibiotic monensin. 3.
Coupling of precursors and transformation to monensin
David B. Collum, John H. McDonald , III, W. Clark Still;
J. Am. Chem. Soc.; 1980; 102(6); 2120-2121
1d. Monensin.
W. C. Still
in 'Classics in total synthesis : targets, strategies, methods', 227-248. /
K.C. Nicolaou and E.J. Sorensen ; with a foreword by E.J. Corey, 1996.
Ch242 RESERVE MIL-8
References for 11/09/05
1. Stereoselective aldol condensation. Use of chiral boron enolates
Satoru Masamune, William Choy, Kerdesky Francis A. J., Barbara Imperiali;
J. Am. Chem. Soc.; 1981; 103(6); 1566-1568
1b. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALDOL REACTIONS VIA ALPHA-SILYL KETONES,
ASYMMETRIC-SYNTHESIS OF THE AGGREGATION PHEROMONE SITOPHILURE
ENDERS D, LOHRAY BB
Angew. Chem. Int. Ed. Engl.; 1988; 27(4); 581-583
MIL-8 Ch242 Reserve
2a. Enantioselective aldol condensations. 2.
Erythro-selective chiral aldol condensations via boron enolates
D. A. Evans, J. Bartroli, T. L. Shih;
J. Am. Chem. Soc.; 1981; 103(8); 2127-2129
2b. STEREOSELECTIVE REACTIONS OF CHIRAL ENOLATES -
APPLICATION TO THE SYNTHESIS OF (+)-PRELOG-DJERASSI LACTONIC ACID
EVANS DA, BARTROLI J
Tetrahedron Lett.; 1982; 23(8); 807-810
MIL-8 Ch242 Reserve
2c. Asymmetric alkylation reactions of chiral imide enolates.
A practical approach to the enantioselective synthesis of .alpha.-substituted carboxylic acid derivatives
D. A. Evans, M. D. Ennis, D. J. Mathre;
J. Am. Chem. Soc.; 1982; 104(6); 1737-1739
3a. Diastereoselective Aldol Reaction with an Acetate Enolate:
2,6-Bis(2-isopropylphenyl)-3,5-dimethylphenol as an Extremely Effective Chiral Auxiliary
Susumu Saito, Keiko Hatanaka, Taichi Kano, Hisashi Yamamoto
Angew. Chem. Int. Ed.; 1998; 37; 3378-81
3b. Acyclic stereoselection. 54.
Extending the scope of the Evans asymmetric aldol reaction:
preparation of anti and "non-Evans" syn aldols
Michael A. Walker, Clayton H. Heathcock;
J. Org. Chem.; 1991; 56(20); 5747-5750
4. ( + )-(7aS)-7a-METHYL-2,3,7,7a-TETRAHYDRO-1 H-INDENE-1,5-(6H)-DIONE
Zoltan G. Hajos and David R. Parrish
Organic Syntheses; CV 7; 363-368
Organic Syntheses; 63; 26-36
5a. Total Synthesis of Macrolactin A with Versatile Catalytic,
Enantioselective Dienolate Aldol Addition Reactions
Yuntae Kim, Robert A. Singer, Erick M. Carreira
Angew. Chem. Int. Ed., 1998, 37, 1261-63
5b. Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates:
A Chiral Tridentate Chelate as a Ligand for Titanium(IV)
Erick M. Carreira, Robert A. Singer, Wheeseong Lee;
J. Am. Chem. Soc.; 1994; 116(19); 8837-8838
5c. Catalytic, Enantioselective Dienolate Additions to Aldehydes:
Preparation of Optically Active Acetoacetate Aldol Adducts
Robert A. Singer, Erick M. Carreira;
J. Am. Chem. Soc.; 1995; 117(49); 12360-12361
References for 11/07/05
1. The Stereochemistry of the Ivanov and Reformatsky Reactions. I
Howard E. Zimmerman, Marjorie D. Traxler;
J. Am. Chem. Soc.; 1957; 79(8); 1920-1923
2a. Major effect of the leaving group in dialkylboron chlorides and triflates in controlling the stereospecific conversion of ketones into either [E]- or [Z]-enol borinates
Herbert C. Brown, Raj K. Dhar, Raman K. Bakshi, Paul K. Pandiarajan, Bakthan Singaram;
J. Am. Chem. Soc.; 1989; 111(9); 3441-3442
2b. Enolboration. 4.
An examination of the effect of the leaving group (X) on the stereoselective enolboration of ketones with various R2BX/triethylamine.
New reagents for the selective generation of either Z or E enol borinates from representative ketones
Herbert C. Brown, Kumaraperumal Ganesan, Raj K. Dhar;
J. Org. Chem.; 1993; 58(1); 147-153
3a. ACYCLIC STEREOSELECTION .27.
SIMPLE DIASTEREOSELECTION IN THE LEWIS ACID MEDIATED REACTIONS OF ENOLSILANES WITH ALDEHYDES
HEATHCOCK CH, HUG KT, FLIPPIN LA
TETRAHEDRON LETTERS 1984, 25(52),5973-5976
Ch242 Reserve MIL-8
3b. Acyclic stereoselection. 54.
Extending the scope of the Evans asymmetric aldol reaction: preparation of anti and "non-Evans" syn aldols
Michael A. Walker, Clayton H. Heathcock;
J. Org. Chem.; 1991; 56(20); 5747-5750
References for 11/04/05 - Synthesis Friday (Manzamines) - Week 6
1a. The First Total Syntheses of Ircinol A, Ircinal A, and Manzamines A and D
Winkler, J. D.; Axten, J. M.;
J. Am. Chem. Soc.; 1998; 120(25); 6425-6426
Supporting Information
1b. Stereoselective Synthesis of the Tetracyclic Core of Manzamine via the Vinylogous Amide Photocycloaddition Cascade.
Jeffrey D. Winkler, Jeffrey Axten ... K. N. Houk
Tetrahedron; 1998; 54(25), 7045-7056
1c. Ircinals A and B from the Okinawan marine sponge Ircinia sp.:
plausible biogenetic precursors of manzamine alkaloids
Kazuhiko Kondo, Hideyuki Shigemori, Yumiko Kikuchi, Masami Ishibashi, Takuma Sasaki, Junichi Kobayashi;
J. Org. Chem.; 1992; 57(8); 2480-2483
References for 11/02/05
1a. The ester enolate Claisen rearrangement.
Stereochemical control through stereoselective enolate formation
Robert E. Ireland, Richard H. Mueller, Alvin K. Willard;
J. Am. Chem. Soc.; 1976; 98(10); 2868-2877
1b. An analysis of the diastereomeric transition state interactions for the kinetic deprotonation of acyclic carbonyl derivatives with lithium diisopropylamide.
Narula, Acharan S..
Tetrahedron Lett. (1981), 22(41), 4119-22.
MIL-8 Ch242 Reserve
1c. Stereochemical control in the ester enolate Claisen rearrangement.
1. Stereoselectivity in silyl ketene acetal formation
Robert E. Ireland, Peter Wipf, Joseph D. Armstrong , III;
J. Org. Chem.; 1991; 56(2); 650-657
2a. Lithium diisopropylamide mixed aggregates:
structures and consequences on the stereochemistry of ketone enolate formation
Angela S. Galiano-Roth, ... David B. Collum;
J. Am. Chem. Soc.; 1991; 113(13); 5053-5055
2b. Sterically shielded secondary N-tritylamines and N-tritylamide bases,
readily available and useful synthetic reagents.
Jakob Busch-Petersen and E. J. Corey
Tetrahedron Lett. (2000), 41(15), 2515-2518
3a. A New Method for the Alkylation of Ketones and Aldehydes:
the C-Alkylation of the Magnesium Salts of N-Substituted Imines
Gilbert Stork, Susan R. Dowd;
J. Am. Chem. Soc.; 1963; 85(14); 2178-2180
3b. Alkylation of Ketones and Aldehydes via their Nitrogen Derivatives.
Whitesell, James K.; Whitesell, Marilyn A.
Synthesis; 1983, (7), 517-536
4a. An asymmetric synthesis of chiral 4,4-disubstituted cyclohexenones in high enantiomeric purity
A. I. Meyers, Bruce A. Lefker, Klaus T. Wanner, R. Alan Aitken;
J. Org. Chem.; 1986; 51(10); 1936-1938
4b. Chiral bicyclic lactams:
useful precursors and templates for asymmetric syntheses
A. I. Meyers and Gregory P. Brengel
Chem. Commun., 1997, (1), 1-8
4c. Alkylation of chiral hydrazones.
Enders, Dieter.
Asymmetric Synth. (1984), 3, 275-339.
MIL-8 Ch242 Reserve
4d. Asymmetric alkylation reactions of chiral imide enolates.
A practical approach to the enantioselective synthesis of .alpha.-substituted carboxylic acid derivatives
D. A. Evans, M. D. Ennis, D. J. Mathre;
J. Am. Chem. Soc.; 1982; 104(6); 1737-1739
Asymmetric acylation reactions of chiral imide enolates.
The first direct approach to the construction of chiral .beta.-dicarbonyl synthons
D. A. Evans, M. D. Ennis, T. Le, N. Mandel, G. Mandel;
J. Am. Chem. Soc.; 1984; 106(4); 1154-1156
References for 10/31/05
1. Synthesis of polycyclic lactam and lactone ethers by intramolecular Reformatskii reactions.
A model for construction of the daphnilactone A ring system
Roger B. Ruggeri, Clayton H. Heathcock
J. Org. Chem.; 1987; 52(26); 5745-5746.
2. Highly stereoselective intramolecular alkylation of an ester enolate:
an approach to the s-hydrindane system.
Ahn, Soon Hyuk; Kim, Deukjoon; Chun, Moon Woo; Chung, Won Keun
Tetrahedron Letters (1986), 27(8), 943-6.
Ch242 MIL-8 Reserve
3. Enantioselective synthesis of an intermediate for the intramolecular Diels-Alder construction of 11-keto steroids.
Stork, Gilbert; Saccomano, Nicholas A.
Tetrahedron Letters (1987), 28(19), 2087-90.
Ch242 MIL-8 Reserve
4. Regiospecific alkylation of cyclic .beta.-diketone enol ethers.
General synthesis of 4-alkylcyclohexenones
Gilbert Stork, Rick L. Danheiser
J. Org. Chem.; 1973; 38(9); 1775-1776.
References for 10/28/05 - Week 5
1. Stereochemistry of hydroboration of .alpha.-chiral olefins and reduction of .alpha.-chiral ketones.
An unusual anti-Cram selectivity with dialkylboranes
M. Mark Midland, Young C. Kwon;
J. Am. Chem. Soc.; 1983; 105(11); 3725-3727
1a. THEORETICAL-STUDIES OF STEREOSELECTIVE HYDROBORATIONS
HOUK KN, RONDAN NG, WU YD, METZ JT, PADDONROW MN
TETRAHEDRON, 1984, 40(12). 2257-2274
MIL-8 RESERVE CH 242
2. HIGHLY ENANTIOSELECTIVE REDUCTION OF ALKYNYL KETONES BY A BINAPHTHOL-MODIFIED ALUMINUM-HYDRIDE REAGENT -
ASYMMETRIC-SYNTHESIS OF SOME INSECT PHEROMONES
NISHIZAWA M, YAMADA M, NOYORI R
TETRAHEDRON LETTERS, 1981, 22(3), 247-250
MIL-8 RESERVE CH 242
3a. Organoboron compounds in organic synthesis. 3.
Mechanism of asymmetric reduction of dialkyl ketones with (R,R)-2,5-dimethylborolane
Satoru Masamune, Robert M. Kennedy, John S. Petersen, K. N. Houk, Yun Dong Wu;
J. Am. Chem. Soc.; 1986; 108(23); 7404-7405
3b. Organoboron compounds in organic synthesis. 2.
Asymmetric reduction of dialkyl ketones with (R,R)- or (S,S)-2,5-dimethylborolane
Toshiro Imai ... Satoru Masamune;
J. Am. Chem. Soc.; 1986; 108(23); 7402-7404
4. ASYMMETRIC REDUCTION OF AROMATIC KETONES WITH THE REAGENT PREPARED FROM (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL AND BORANE
ITSUNO S, ITO K, HIRAO A, NAKAHAMA S
J. CHEM. SOC. CHEM. COMMUN. 1983, (8), 469-470
5a. Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines.
Mechanism and synthetic implications
E. J. Corey, Raman K. Bakshi, Saizo Shibata;
J. Am. Chem. Soc.; 1987; 109(18); 5551-5553
5b. Reduction of Carbonyl Compounds with Chiral Oxazaborolidine Catalysts:
A New Paradigm for Enantioselective Catalysis and a Powerful New Synthetic Method
Elias J. Corey, Christopher J. Helal
Angew. Chem. Int. Ed. 1998, 37(15), 1986-2012
6. ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE IN THE TOTAL SYNTHESIS OF FORSKOLIN
COREY EJ, JARDINE PD, MOHRI T
TETRAHEDRON LETTERS, 1988, 29(49), 6409-6412
MIL-8 RESERVE CH 242
7. "Discoveries Missed, Discoveries Made:
Two Case Studies of Creativity in Chemistry"
in Chemical creativity, Chapter 2, p. 9-32.
Jerome A. Berson, 1999.
MIL-8 RESERVE CH 242
8a. Asymmetric hydrogenation of .beta.-keto carboxylic esters.
A practical, purely chemical access to .beta.-hydroxy esters in high enantiomeric purity
Ryoji Noyori ... Susumu Akutagawa;
J. Am. Chem. Soc.; 1987; 109(19); 5856-5858
8b. Metal-Ligand Bifunctional Catalysis:
A Nonclassical Mechanism for Asymmetric Hydrogen Transfer between Alcohols and Carbonyl Compounds
Noyori, R.; Yamakawa, M.; Hashiguchi, S.;
J. Org. Chem.; 2001; 66(24); 7931-7944
8c. Asymmetric Catalysis by Architectural and Functional Molecular Engineering:
Practical Chemo- and Stereoselective Hydrogenation of Ketones
Ryoji Noyori, Takeshi Ohkuma
Angew. Chem. Int. Ed., 2001, 40(1), 40-73
References for 10/26/05
1a. Hydroboration
Brown, H.C., 1962
Mil-8 Reserves Ch242
1b. Transition-metal promoted hydroborations of alkenes,
emerging methodology for organic transformations
Kevin Burgess, Michael J. Ohlmeyer;
Chem. Rev.; 1991; 91(6); 1179-1191
1c. From little acorns to tall oaks - from boranes through organoboranes
H.C. Brown
Nobel Lecture, December 8, 1979
2a. The Stereochemistry of Hydride Reductions.
William G. Dauben, Gerhard J. Fonken, Donald S. Noyce;
J. Am. Chem. Soc.; 1956; 78(11); 2579-2582
2b. Stereochemistry of organometallic compound addition to ketones
E.C. Ashby and J.T. Laemmle
Chem. Rev.; 1975; 75(4); 521-546
3. Torsional strain involving partial bonds.
The stereochemistry of the lithium aluminum hydride reduction of some simple open-chain ketones.
Cherest, Marc; Felkin, Hugh; Prudent, Nicole.
Tetrahedron Lett. (1968),(18),2199-204.
Mil-8 Reserves Ch242
4a. Studies in Stereochemistry. XXX.
Models for Steric Control of Asymmetric Induction
Donald J. Cram, Karl R. Kopecky;
J. Am. Chem. Soc.; 1959; 81(11); 2748-2755
4b. New synthetic methods.(44).
Chelate- or nonchelate control in addition reactions of chiral a- and b-alkoxycarbonyl compounds.
Reetz, Manfred T.
Angew. Chem. (1984),23(8),556-569.
Mil-8 Reserves Ch242
5a. Highly stereocontrolled reduction of a'-alkoxyenones to give either the threo or erythro allylic 1,2-diol.
Assignment of the threo configuration to the C-15,C-16 diol of pumiliotoxin B.
Overman, Larry E.; McCready, Russell J.
Tetrahedron Lett. (1982), 23(23), 2355-8.
Mil-8 Reserves Ch242
5b. Rapid-injection nuclear magnetic resonance investigation of the reactivity of .alpha.- and .beta.-alkoxy ketones with dimethylmagnesium: kinetic evidence for chelation
Stephen V. Frye, Ernest L. Eliel, Roland Cloux;
J. Am. Chem. Soc.; 1987; 109(6); 1862-1863
5c. Stereoselective reduction of b-hydroxy ketones to 1,3-diols.
Highly selective 1,3-asymmetric induction via boron chelates.
Narasaka, Koichi; Pai, Fong Chang.
Tetrahedron (1984), 40(12), 2233-8.
Mil-8 Reserves Ch242
5d. 1,3-syn-Diastereoselective reduction of b-hydroxy ketones utilizing alkoxydialkylboranes.
Chen, Kau Ming ... Shapiro, Michael J.
Tetrahedron Letters (1987), 28(2), 155-8.
Mil-8 Reserves Ch242
5e. Stereoselective reduction of a-methyl-b-hydroxy ketones with zinc borohydride.
Nakata, Tadashi; Tani, Yoichiro; Hatozaki, Masayoshi; Oishi, Takeshi.
Chem. Pharm. Bull. (1984), 32(4), 1411-15.
Mil-8 Reserves Ch242
5f. Stereoselective synthesis of syn-1,3-diols.
Mohr, Peter.
Tetrahedron Letters (1991), 32(20), 2219-22.
Mil-8 Reserves Ch242
6. Samarium-catalyzed intramolecular Tishchenko reduction of .beta.-hydroxy ketones.
A stereoselective approach to the synthesis of differentiated anti 1,3-diol monoesters
David A. Evans, Amir H. Hoveyda;
J. Am. Chem. Soc.; 1990; 112(17); 6447-6449
References for 10/24/05
1. "Asymmetric Catalytic Hydrogenation: Mechanism and Origin of Enantioselection"
in Asymmetric Synthesis, 1985, 5, 41-69.
J. Halpern
MIL-8 Ch242 Reserve
2. Chiral Imidazolylidine Ligands for Asymmetric Hydrogenation of Aryl Alkenes
Mark T. Powell ... Kevin Burgess
J. Am. Chem. Soc. 2001, 123, 8878 - 8879.
3. Ate complex from diisobutylaluminum hydride and n-butyllithium as a powerful and selective reducing agent for the reduction of selected organic compounds containing various functional groups
Sunggak Kim, Kyo Han Ahn;
J. Org. Chem.; 1984; 49(10); 1717-1724.
References for 10/21/05 - Synthesis Friday (Hapalindole G) - Week 4
1. Stereocontrolled Synthesis of (-)-Hapalindole G
Tohru Fukuyama, Xiaoqi Chen;
J. Am. Chem. Soc.; 1994; 116(7); 3125-3126.
2. "Structure-based and topological strategies" in
The Logic of Chemical Synthesis, p.33-46.
E.J. Corey and X.M. Cheng
MIL-8 Ch242 Reserve Shelf
3. Total synthesis of natural products: The "Chiron" approach
Stephen Hanessian, 1983
MIL-8 Ch242 Reserve Shelf
4. "Readily Available Chiral Carbon Fragments and Their Use in Synthesis"
in Asymmetric Synthesis, Vol. 4 pp. 1-226, 1984
J.W. Scott
MIL-8 Ch242 Reserve Shelf
References for 10/18/05
1a. Desulfurization with Raney Nickel
G.R. Pettit
Org. React. 1962, 12, 356-529
MIL-8 REF QD 251 O7 v.12
1b. The Action of Raney Nickel on Organic Sulfur Compounds.
Heinrich Hauptmann and Wolfgang Ferdinand Walter
Chem. Rev. 1962, 62, 347-404
2. Hydrogenation of organic compounds using homogeneous catalysts
Robert E. Harmon, S. K. Gupta, and D. J. Brown
Chem. Rev. 1973, 73, 21 - 52
3a. Directed homogeneous hydrogenation
J.M. Brown
Angew. Chem. Int. Ed. Engl. 1987, 26, 190-203
MIL-8 Ch242 Reserve Shelf
3b. Iridium compounds in catalysis
Robert Crabtree;
Acc. Chem. Res.; 1979; 12(9); 331-337
3c. Stereochemical control of reductions. IV.
Control of hydrogenation stereochemistry by intramolecular anionic coordination to homogeneous catalysts
Hugh W. Thompson, Eugene McPherson;
J. Am. Chem. Soc.; 1974; 96(19); 6232-6233
3d. Occurrence and origin of a pronounced directing effect of a hydroxyl group in hydrogenation with [Ir(cod)P(C6H11)3(py)]PF6
Robert H. Crabtree, Mark W. Davis;
Organometallics; 1983; 2(5); 681-682
3e. Stereocontrol in homogeneous catalytic hydrogenation via hydroxyl group coordination
Gilbert Stork, Daniel E. Kahne;
J. Am. Chem. Soc.; 1983; 105(4); 1072-1073
3f. Methods for stereospecific synthesis
E.J. Corey
Tetrahedron Lett. 1984, 25(2), 149-152
MIL-8 Ch242 Reserve Shelf
4a. Asymmetric Hydrogenations (Nobel Lecture)
William S. Knowles
Angew. Chem. Int. Ed. 2002, 41(12), 2008-2022
MIL-8 Ch242 Reserve Shelf
4b. Asymmetric Catalysis: Science and Opportunities (Nobel Lecture)
Ryoji Noyori
Angew. Chem. Int. Ed. 2002, 41(12), 1998-2007
MIL-8 Ch242 Reserve Shelf
4c. Asymmetric hydrogenation
I. Ojima in 'Catalytic Asymmetric Synthesis', 2nd ed. 2000. pages 1-110.
MIL-8 Ch242 Reserve Shelf
4d. Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts
Grazia Zassinovich, Giovanni Mestroni, Serafino Gladiali;
Chem. Rev.; 1992; 92(5); 1051-1069
5a. Asymmetric Transfer Hydrogenation Catalyzed by Chiral Ruthenium Complexes
Noyori, R.; Hashiguchi, S.;
Acc. Chem. Res.; (Article); 1997; 30(2); 97-102
5b. Enantioselective hydrogenation of olefins with Iridium-phosphanodihydrooxazole catalysts
A. Lightfoot ... A. Pfaltz
Angew. Chem. Int. Ed. Engl. 1998
MIL-8 Ch242 Reserve Shelf
References for 10/17/05
1a. Vanadium-catalyzed epoxidations. 2.
Highly stereoselective epoxidations of acyclic homoallylic alcohols predicted by a detailed transition-state model
Edward D. Mihelich, Karen Daniels, David J. Eickhoff
J. Am. Chem. Soc.; 1981; 103(25); 7690-7692.
1b. Synthetic studies on polyether antibiotics. II.
Stereoselective syntheses of epoxides of bishomoallylic alcohols
T. Fukuyama ... Y. Kishi.
Tetrahedron Lett. 1978, (31), 2741-2744
MIL-8 Ch242 Reserve Shelf
2. Development of the Directed Dihydroxylation Reaction
Donohoe, Timothy J.
SynLett 2002, (8), 1223-1232
3. Searching for New Reactivity (Nobel Lecture)
K. Barry Sharpless
Angew. Chem. Int. Ed. 2002, 41(12), 2024-2032
MIL-8 Ch242 Reserve Shelf
4a. The first practical method for asymmetric epoxidation
Tsutomu Katsuki, K. Barry Sharpless;
J. Am. Chem. Soc.; 1980; 102(18); 5974-5976.
4b. On the origin of enantioselectivity in the Katsuki-Sharpless epoxidation procedure
E. J. Corey
J. Org. Chem.; 1990; 55(6); 1693-1694.
5. Double asymmetric synthesis and a new strategy for stereochemical control in organic synthesis.
S. Masamune; L.R. Sita
Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30
MIL-8 Ch242 Reserve Shelf
6. Kinetic resolution of racemic allylic alcohols by enantioselective epoxidation.
A route to substances of absolute enantiomeric purity?
Victor S. Martin, Scott S. Woodard, Tsutomu Katsuki, Yasuhiro Yamada, Masonari Ikeda, K. Barry Sharpless
J. Am. Chem. Soc.; 1981; 103(20); 6237-6240.
7a. Highly enantioselective epoxidation catalysts derived from 1,2-diaminocyclohexane
Eric N. Jacobsen, Wei Zhang, Alexander R. Muci, James R. Ecker, Li Deng
J. Am. Chem. Soc.; 1991; 113(18); 7063-7064.
7b. A practical, highly enantioselective synthesis of the taxol side chain via asymmetric catalysis.
Li Deng, Eric N. Jacobsen
J. Org. Chem.; 1992; 57(15); 4320-4323.
7c. The Mechanistic Basis for Electronic Effects on Enantioselectivity in the (salen)Mn(III)-Catalyzed Epoxidation Reaction
Palucki, M.; Finney, N. S.; Pospisil, P. J.; Guler, M. L.; Ishida, T.; Jacobsen, E. N.
J. Am. Chem. Soc.; (Article); 1998; 120(5); 948-954.
7d. On the viability of oxametallacyclic intermediates in the (salen)Mn-catalyzed asymmetric epoxidation.
Finney, Nathaniel S.; Jacobsen, Eric N.
Angew. Chem., Int. Ed. Engl. (1997), 36(16), 1720-1723.
MIL-8 Ch242 Reserve Shelf
7e. Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins
Bridget D. Brandes, Eric N. Jacobsen;
J. Org. Chem.; 1994; 59(16); 4378-4380.
7f. An Efficient Asymmetric Epoxidation Method for trans-Olefins Mediated by a Fructose-Derived Ketone
Tu, Y.; Wang, Z.-X.; Shi, Y.
J. Am. Chem. Soc.; (Communication); 1996; 118(40); 9806-9807.
8a. Toward an Understanding of the High Enantioselectivity in the Osmium-Catalyzed Asymmetric Dihydroxylation (AD). 1.
Kinetics
Hartmuth C. Kolb, Pher G. Andersson, K. Barry Sharpless
J. Am. Chem. Soc.; 1994; 116(4); 1278-1291.
8b. Asymmetric dihydroxylation via ligand-accelerated catalysis.
Eric N. Jacobsen, K. Barry Sharpless
J. Am. Chem. Soc.; 1988; 110(6); 1968-1970.
9a. From Styrenes to Enantiopure -Arylglycines in Two Steps.
Reddy, K. L.; Sharpless, K. B.
J. Am. Chem. Soc.; (Article); 1998; 120(6); 1207-1217.
9b. Reversal of Regioselection in the Sharpless Asymmetric Aminohydroxylation of Aryl Ester Substrates.
Morgan, A. J.; Masse, C. E.; Panek, J. S.
Org. Lett.; (Communication); 1999; 1(12); 1949-1952.
Supporting Information
References for 10/14/05 - Synthesis Friday (Nicandrenones) - Week 3
1a. Enantioselective Total Synthesis of Nicandrenones
Stoltz, B. M.; Kano, T.; Corey, E. J.
J. Am. Chem. Soc.; (Communication); 2000; 122(37); 9044-9045.
Supporting Information
1b. Cuprous Chloride Accelerated Stille Reactions.
A General and Effective Coupling System for Sterically Congested Substrates and for Enantioselective Synthesis
Han, X.; Stoltz, B. M.; Corey, E. J.
J. Am. Chem. Soc.; (Article); 1999; 121(33); 7600-7605.
Supporting Information
1c. Mechanistic Insights into the Factors Determining Exo-Endo Selectivity in the Lewis Acid-Catalyzed Diels-Alder Reaction of 1,3-Dienes with 2-Cycloalkenones
Ge, M.; Stoltz, B. M.; Corey, E. J.
Org. Lett.; (Communication); 2000; 2(13); 1927-1929.
References for 10/12/05
1a. Aspects of stereochemistry. I.
Stereospecificity in formation of epoxides from cyclic allylic alcohols.
Henbest, H. B.; Wilson, R. A. L.
J. Chem. Soc. 1957, (4), 1958-65.
1b. Metal-catalyzed, highly selective oxygenations of olefins and acetylenes with tert-butyl hydroperoxide.
Practical considerations and mechanisms.
Sharpless, K. Barry; Verhoeven, Thomas R.
Aldrichimica Acta 1979, 12(4), 63-74.
MIL-8 Ch242a Reserve Shelf
1c. Transition state structure for peracid epoxidation.
Secondary deuterium isotope effects
Robert P. Hanzlik, Greg O. Shearer
J. Am. Chem. Soc.; 1975; 97(18); 5231-5233.
1d. Syn-stereoselective epoxidation of allylic ethers using CF3CO3H
McKittrick, B.A.
Tetrahedron Lett. 1985, 26(40), 4895-4898.
MIL-8 Ch242a Reserve Shelf
2a. The conformation of the steroid nucleus.
Barton, D. H. R.
Experientia 1950; 6; 316-20.
MIL-8 Ch242a Reserve Shelf
2b. Eliel, E.L.
Stereochemistry of organic compounds;
with a chapter on stereoselective synthesis
Wiley & Sons, c1994
MIL-1 Reserve (QD481 .E525 1994)
MIL-8 Reserve Ch242
2c. The torsional potential function for butane.
Allinger, N. L.; Profeta, S., Jr.
J. Comput. Chem. 1980, 1(2), 181-4.
MIL-8 Ch242a Reserve Shelf
3. Allylic 1,3-strain as a controlling factor in stereoselective transformations
Reinhard W. Hoffmann
Chem. Rev.; 1989; 89(8); 1841-1860.
References for 10/10/05
1. Preparation, properties, and reactions of carbonyl oxides
William H. Bunnelle;
Chem. Rev.; 1991; 91(3);335-362.
2. Total synthesis of strychnine.
Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K.
Tetrahedron (1963), 19 247-88. (unique ozone oxidation described on p.252)
MIL-8 Ch242a Reserve Shelf
3. The Dess-Martin Periodinane:
1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one
Boeckman, R.K.; Shao, P.C.; and Mullins, J.J.
Org. Synth. 77,141-152.
4. Selective oxidation of aldehydes to carboxylic acids with sodium chlorite-hydrogen peroxide
Enrico Dalcanale, Fernando Montanari;
J. Org. Chem.; 1986; 51(4); 567-569.
5. Design and Implementation of an Efficient Synthetic Approach to Pyranosylated Indolocarbazoles:
Total Synthesis of (+)-RK286c, (+)-MLR-52, (+)-Staurosporine, and (-)-TAN-1030a
John L. Wood, Brian M. Stoltz, Steven N. Goodman, and Kenolisa Onwueme
J. Am. Chem. Soc.; 1997; 119(41); 9051-9052.
6. Application of the allylic diazene rearrangement:
synthesis of the enediyne-bridged tricyclic core of dynemicin A
John L. Wood, John A. Porco , Jr., Jack Taunton, Angela Y. Lee, Jon Clardy, Stuart L. Schreiber;
J. Am. Chem. Soc.; 1992; 114(14); 5898-5900.
7. Oxidation of Primary Alcohols to Carboxylic Acids with Sodium Chlorite Catalyzed by TEMPO and Bleach
Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J.
J. Org. Chem.; (Technical Note); 1999; 64(7); 2564-2566.
References for 10/07/05 - Synthesis Friday (Naphthyridinomycin) - Week 2
1a. The Total Synthesis of (+/-)-Naphthyridinomycin. 1.
Preparation of a key tricyclic lactam intermediate.
D. A. Evans, S.A. Biller
Tetrahedron Lett. 1985, 26 (16): 1907-1910
MIL-8 Ch 242A Reserve Shelf
1b. The Total Synthesis of (+/-)-Naphthyridinomycin. 2.
Construction of the pentacyclic carbon skeleton.
D. A. Evans, S.A. Biller
Tetrahedron Lett. 1985, 26 (16): 1911-1914.
MIL-8 Ch 242A Reserve Shelf
1c. Stereoselective synthesis of (.+-.)-cyanocycline
David A. Evans, Carl R. Illig, John C. Saddler;
J. Am. Chem. Soc.; 1986; 108(9); 2478-2479.
1d. An approach to the total synthesis of (+)-naphthyridinomycin A.
Biller, Scott Adams.
Caltech theses ; 1982.
http://etd.caltech.edu/etd/available/etd-10312002-152412/
References for 10/05/05
A Mechanistically Guided Design Leads to the Synthesis of an Efficient and Practical New Reagent for the Highly Enantioselective,
Catalytic Dihydroxylation of Olefins
Huang, J.; Corey, E. J.;
Org. Lett.; 2003; 5(19); 3455-3458.
1a. An improved catalytic OsO4 oxidation of olefins ...
V. VanRheenen, et. al.
Tetrahedron Letters 1976,(23),1973-1976
MIL-8 Ch242a Reserve Shelf
1b. Asymmetric dihydroxylation via ligand-accelerated catalysis
Eric N. Jacobsen, … K. Barry Sharpless;
J. Am. Chem. Soc.; 1988 ;110 (6); 1968-1970.
1c. Kinetic role of the alkaloid ligands in asymmetric catalytic dihydroxylation
Eric N. Jacobsen … K. Barry Sharpless
J. Am. Chem. Soc.; 1989 ;111 (2); 737-739.
1d. Stereochemical control in Wittig olefin synthesis.
Preparation of the pink bollworm sex pheromone mixture, gossyplure
Richard J. Anderson, Clive A. Henrick;
J. Am. Chem. Soc.; 1975; 97(15); 4327-4334.
2a. Transition-metal peroxide reactions.
Synthesis of .alpha.-hydroxycarbonyl compounds from enolates
E. Vedejs, D. A. Engler, J. E. Telschow;
J. Org. Chem.; 1978; 43(2); 188-196.
2b. Total syntheses of di- and tri-O-methyl dynemicin A methyl esters
Jack Taunton, John L. Wood, Stuart L. Schreiber;
J. Am. Chem. Soc.; 1993; 115(22); 10378-10379.
3a. Palladium-Catalyzed Oxidation of Primary and Secondary Allylic and Benzylic Alcohols
Peterson, K. P.; Larock, R. C.;
J. Org. Chem.; 1998; 63(10); 3185-3189.
3b. A simple effective new palladium-catalyzed conversion of enol silanes to enones and enals.
Larock, R. C., et.al.
Tetrahedron Letters (1995),36(14),2423-6.
3c. Enantioselective Total Synthesis of Nicandrenones
Stoltz, B. M.; Kano, T.; Corey, E. J.;
J. Am. Chem. Soc.; 2000; 122(37); 9044-9045.
3d. Cyclization reactions via oxo-.pi.-allylpalladium(II) intermediates
Yoshihiko Ito, ... Takeo Saegusa;
J. Am. Chem. Soc.; 1979; 101(2); 494-496.
4. Selenium dioxide oxidation.
Rabjohn, Norman.
Org. React. (N. Y.) (1976),24,261-415.
MIL-8 REF QD 251 O7 v.24
5a. Activated dimethyl sulfoxide:
useful reagents for synthesis.
Mancuso, Anthony J.; Swern, Daniel.
Synthesis (1981), (3),165-85.
5b. Oxidation of alcohols by activated dimethyl sulfoxide and related reactions:
an update.
Tidwell, Thomas T.
Synthesis (1990), (10),857-70.
5c. Oxidation of alcohols to carbonyl compounds via alkoxysulfonium ylides:
the Moffat, Swern, and related oxidations.
Tidwell, Thomas T.
Org. React. (N. Y.) (1990),39,297-572.
MIL-8 REF QD 251 O7 v.24
6. A one-pot conversion of olefins to .alpha.,.beta.-unsaturated carbonyl compounds.
An easy synthesis of 2-cyclopentenone and related compounds
Edward D. Mihelich, David J. Eickhoff;
J. Org. Chem.; 1983; 48(22); 4135-4137.
References for 10/03/05
1a. The Mechanisms of Chromic Acid Oxidations.
Westheimer, F.H.
Chem. Rev.; 1949; 45(3); 419-451.
1b. Oxidation by Chromic Acid and Chromyl Compounds in
"Oxidation in Organic Chemistry", Part A, 69-185, 1965.
Wiberg, K.B.
MIL-8 Reserve (Ch 154 shelf).
1c. The endiandric acid cascade. Electrocyclizations in organic synthesis. 3.
"Biomimetic" approach to endiandric acids A-G. Synthesis of precursors
K. C. Nicolaou, et.al.
J. Am. Chem. Soc.; 1982; 104(20); 5558-5560.
1d. A Novel Chromium Trioxide Catalyzed Oxidation of Primary Alcohols to the Carboxylic Acids
Zhao Mangzhu, et.al.
TETRAHEDRON LETTERS 1998, 39(30),5323-5326
2a. Pyridinium chlorochromate.
Efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds.
Corey, E. J.; Suggs, J. W.
Tetrahedron Lett. 1975, (31),2647-50.
MIL-8 Ch242a Reserve Shelf
2b. Pyridinium Chlorochromate:
A Versatile Oxidant in Organic Synthesis
Piancatelli, G., et.al.
Synthesis 1982, (4), 245-258
2c. Pyridinium Chlorochromate Adsorbed on Alumina as a Selective Oxidant for Primary and Secondary Alcohols.
Cheng, Yu-Shia, et.al.
Synthesis 1980, (3), 223-224
2d. Direct oxidation of tertiary allylic alcohols.
A simple and effective method for alkylative carbonyl transposition
William G. Dauben, et.al.
J. Org. Chem.; 1977; 42(4); 682-685.
2e. Convenient synthesis of (S)-(-)-pulegone from (-)-citronellol
E. J. Corey, et.al.
J. Org. Chem.; 1976; 41(2); 380-381.
2f. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media.
Corey, E. J.; Schmidt, G.
Tetrahedron Lett. 1979, (5),399-402.
MIL-8 Ch242a Reserve Shelf
New oxidative systems for alcohols:
Molecular sieves with chromium(VI) reagents
J. Herscovici, … K. Antonakis.
J. Chem. Soc. Perkin Trans. 1 1982 (9), 1967-1973.
Pyridinium dichromate oxidation.
Modifications enhancing its synthetic utility.
S. Czernecki, … K. Vijayakumaran.
Tetrahedron Lett. 1985, 26 (14), 1699-1702.
MIL-8 Ch242a Reserve Shelf
Modified pyridinium dichromate oxidation.
A facile synthesis of the key 3-keto sugar intermediate for L-daunosamine.
S. Szernecki, … K. Vijayakumaran.
Synthetic Commun. 1986, 16 (1), 11-18
MIL-8 Ch242a Reserve Shelf
3a. Improved procedure for the potassium permanganate oxidation of olefins to cis-1,2-glycols by use of phase transfer catalysis.
Weber, William P.; Shepherd, James P..
Tetrahedron Lett. (1972), (48), 4907-8.
MIL-8 Ch242a Reserve Shelf
3b. Model studies of terpene biosynthesis.
Synthesis and absolute configuration of (+)-trans-2,2-dimethyl-3-(2'-methylpropenyl)cyclobutanol.
Oliver J. Muscio, C. Dale Poulter;
J. Org. Chem.; 1974 ;39 (22); 3288-3291.
3c. Steroids. LXVII.1
The Decarboxylation of Unsaturated Steroidal Acids.
Synthesis of 17-Epitestosterone and of 17-Methylepitestosterone.
Franz Sondheimer, et.al.
J. Am. Chem. Soc. 1955, 77,4145-4149.
3d. The classical permanganate ion.
Still a novel oxidant in organic synthesis
A. Fatiadi;
Synthesis 1987 (2), 85-127.
4a. A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds
Carllsen, P.H.J. … Sharpless, K.B.;
J. Org. Chem.; 1981; 46(19); 3936-3938.
4b. Preparation and use of tetrabutylammonium perruthenate (TBAP reagent) and tetrapropylammonium perruthenate (TPAP reagent) as new catalytic oxidants for alcohols.
Griffith, William P., et.al.
J. Chem. Soc., Chem. Commun. (1987), (21), 1625-7.
4c. Further investigations of the type II Diels-Alder route to the bicyclic core of esperamicin/calichemicin reveal a regiochemical misassignment: meta versus para selectivity.
Schreiber, Stuart L., et.al.
Tetrahedron Lett. (1989), 30(4), 433-6.
MIL-8 Ch242a Reserve Shelf
References for 9/30/05 - Synthesis Friday
(Gibberellic Acid) - Week 1
1a. Stereospecific total
synthesis of gibberellic acid.
A key tricyclic intermediate
E. J. Corey, et.al.;
J. Am. Chem. Soc.; 1978; 100(25); 8031-8034
1b. Stereospecific total
synthesis of gibberellic acid
E. J. Corey, et.al.;
J. Am. Chem. Soc.; 1978; 100(25); 8034-8036
2a. "Multistrategic
Retrosynthetis Analysis of Gibberellic Acid" in
The Logic of Chemical Synthesis, pages
84-86.
MIL-8 Ch242 Reserve Shelf
2b. "Gibberellic Acid"
in
The Logic of Chemical Synthesis, pages
205-211.
MIL-8 Ch242 Reserve Shelf
3. "The Total Synthesis of
Gibberellic Acid" in
Strategies and Tactics in
Organic Synthesis, v.1, pages 21-70.
MIL-8 Ch242 Reserve Shelf
References for 9/28/05
1a. TOTAL SYNTHESIS OF
d,l-LONGIFOLENE
E. J. Corey, et.al.;
J. Am. Chem. Soc.; 1961; 83(5); 1251-1253
1b. Total Synthesis of
Longifolene
E. J. Corey, et.al.;
J. Am. Chem. Soc.; 1964; 86(3); 478-485