PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS BY USING ENZYMES .12. A SYNTHESIS OF NATURAL ALPHA-TOCOPHEROL INTERMEDIATE

被引：28

作者：

SUGAI, T ^{[1
]}

WATANABE, N ^{[1
]}

OHTA, H ^{[1
]}

机构：

[1] KEIO UNIV,DEPT CHEM,HIYOSHI 3-14-1,YOKOHAMA,KANAGAWA 223,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(00)82122-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(S)-(-)-6-Hydroxy-2,5,7,8-tetramethyl-2-chromanmethanol, an intermediate of natural alpha-tocopherol was synthesized from (S)-2-benzyloxy-2-methyl-4-pentenoic acid, which was obtained by the enzymatic hydrolysis of the corresponding racemic methyl ester.

引用

页码：371 / 376

页数：6

共 11 条

[1] 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

[2] 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

[3] 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

[4] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[5]

HUBSCHER J, 1990, HELV CHIM ACTA, V73, P1068, DOI 10.1002/hlca.19900730431

[6] ASYMMETRIC-SYNTHESIS OF A CHROMAN DERIVATIVE (VITAMIN-E PRECURSOR) [J].

SAKITO, Y ;

SUZUKAMO, G .

TETRAHEDRON LETTERS, 1982, 23 (47) :4953-4954

[7]

SMITH LI, 1941, J ORG CHEM, V6, P230

[8] PREPARATION OF CHIRAL COMPOUND USING ENZYMES .4. A SYNTHESIS OF (R)-(-)-MEVALONOLACTONE BY THE COMBINATION OF ENZYMATIC AND CHEMICAL METHODS [J].

SUGAI, T ;

KAKEYA, H ;

OHTA, H .

TETRAHEDRON, 1990, 46 (10) :3463-3468

[9] PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS USING ENZYMES .3. ENZYMATIC PREPARATION OF ENANTIOMERICALLY ENRICHED TERTIARY ALPHA-BENZYLOXY ACID-ESTERS - APPLICATION TO THE SYNTHESIS OF (S)-(-)-FRONTALIN [J].

SUGAI, T ;

KAKEYA, H ;

OHTA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4643-4647

[10] AN EFFICIENT SYNTHESIS OF (S)-CHROMANMETHANOL, A VITAMIN-E PRECURSOR [J].

TAKABE, K ;

OKISAKA, K ;

UCHIYAMA, Y ;

KATAGIRI, T ;

YODA, H .

CHEMISTRY LETTERS, 1985, (05) :561-562

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