SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHERYL ACETATE (VITAMIN-E ACETATE) USING [3,3] SIGMATROPIC REARRANGEMENT

被引:54
作者
CHAN, KK
SPECIAN, AC
SAUCY, G
机构
关键词
D O I
10.1021/jo00412a001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:3435 / 3440
页数:6
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共 25 条
[1]   DEHYDRATIONS WITH AROMATIC SULFONYL HALIDES IN PYRIDINE .2. A CONVENIENT METHOD FOR THE PREPARATION OF ESTERS [J].
BREWSTER, JH ;
CIOTTI, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) :6214-6215
[2]   SYNTHETIC STUDIES ON (2R,4'R,8'R)-ALPHA-TOCOPHEROL FACILE SYNTHESES OF OPTICALLY-ACTIVE, SATURATED, ACYCLIC ISOPRENOIDS VIA STEREOSPECIFIC [3,3] SIGMATROPIC REARRANGEMENTS [J].
CHAN, KK ;
COHEN, N ;
DENOBLE, JP ;
SPECIAN, AC ;
SAUCY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3497-3505
[3]   TRANSFER OF CHIRALITY IN [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC ALCOHOLS TO BETA,GAMMA-UNSATURATED AMIDES - PREPARATION OF OPTICALLY-ACTIVE 9-CARBON AND 14-CARBON SATURATED ISOPRENOID SYNTHONS [J].
CHAN, KK ;
SAUCY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3828-3832
[4]  
CHAN KK, 1976, 172ND NAT M AM CHEM
[5]  
CHAN KY, UNPUBLISHED
[6]   SYNTHETIC STUDIES ON 2R,4'R,8'R-ALPHA-TOCOPHEROL - ALTERNATIVE SYNTHESIS OF (2R,6R)-(+)-2,6,10-TRIMETHYLUNDECAN-1-OL, A KEY SIDE-CHAIN SYNTHON [J].
COHEN, N ;
EICHEL, WF ;
LOPRESTI, RJ ;
NEUKOM, C ;
SAUCY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3512-3515
[7]   SYNTHETIC STUDIES ON 2R,4',8'R-ALPHA-TOCOPHEROL - APPROACH UTILIZING SIDE-CHAIN SYNTHONS OF MICROBIOLOGICAL ORIGIN [J].
COHEN, N ;
EICHEL, WF ;
LOPRESTI, RJ ;
NEUKOM, C ;
SAUCY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (22) :3505-3511
[8]  
COREY EJ, 1977, TETRAHEDRON LETT, P1625
[9]   APPLICATION OF CLAISEN REARRANGEMENT TO SYNTHESIS OF TRANS TRISUBSTITUTED OLEFINIC BONDS - SYNTHESIS OF SQUALENE AND INSECT JUVENILE-HORMONE [J].
FAULKNER, DJ ;
PETERSEN, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :553-563
[10]   IMPROVED CARBON-CARBON LINKING BY CONTROLLED COPPER CATALYSIS [J].
FOUQUET, G ;
SCHLOSSE.M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1974, 13 (01) :82-83