IMPROVEMENTS IN THE SYNTHESIS OF A KEY ALPHA-TOCOPHEROL INTERMEDIATE - (S)-(-)-3,4-DIHYDRO-6-HYDROXY-2,5,7,8-TETRAMETHYL-2H-1-BENZOPYRAN-2-ACETIC ACID

被引:20
作者
COHEN, N
BANNER, BL
NEUKOM, C
机构
关键词
D O I
10.1080/00397918208080067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
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页码:57 / 65
页数:9
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[1]  
AKKERMAN JM, 1981, HETEROCYCLES, V15, P797
[2]   TOTAL SYNTHESIS OF NATURAL ALPHA-TOCOPHEROL .4. PREPARATION OF CHROMANE RING-SYSTEM FROM TRIMETHYLHYDROQUINONE AND OPTICALLY-ACTIVE C-4 AND C5 SYNTHONE [J].
BARNER, R ;
SCHMID, M .
HELVETICA CHIMICA ACTA, 1979, 62 (07) :2384-2399
[3]   SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHERYL ACETATE (VITAMIN-E ACETATE) USING [3,3] SIGMATROPIC REARRANGEMENT [J].
CHAN, KK ;
SPECIAN, AC ;
SAUCY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) :3435-3440
[4]   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
[5]   NOVEL TOTAL SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHEROL (VITAMIN-E) - CONSTRUCTION OF CHIRAL CHROMANS FROM AN OPTICALLY-ACTIVE, NON-AROMATIC PRECURSOR [J].
COHEN, N ;
LOPRESTI, RJ ;
SAUCY, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (22) :6710-6716
[6]   STUDIES ON THE TOTAL SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHEROL (VITAMIN-E) - STEREOSPECIFIC CYCLIZATIONS LEADING TO OPTICALLY-ACTIVE CHROMANS [J].
COHEN, N ;
LOPRESTI, RJ ;
NEUKOM, C .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (12) :2445-2450
[7]   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
[8]   STUDIES ON SYNTHESIS OF (2R,4'R,8'R)-ALPHA-TOCOPHEROL ALTERNATIVE SYNTHESES OF 2-CHROMAN-ACETIC ACID INTERMEDIATES [J].
COHEN, N ;
SCOTT, JW ;
BIZZARO, FT ;
LOPRESTI, RJ ;
EICHEL, WF ;
SAUCY, G ;
MAYER, H .
HELVETICA CHIMICA ACTA, 1978, 61 (02) :837-843
[9]   TOTAL SYNTHESIS OF ALL 8 STEREOISOMERS OF ALPHA-TOCOPHERYL ACETATE - DETERMINATION OF THEIR DIASTEREOISOMERIC AND ENANTIOMERIC PURITY BY GAS-CHROMATOGRAPHY [J].
COHEN, N ;
SCOTT, CG ;
NEUKOM, C ;
LOPRESTI, RJ ;
WEBER, G ;
SAUCY, G .
HELVETICA CHIMICA ACTA, 1981, 64 (04) :1158-1173
[10]   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