Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative

被引：24

作者：

Chênevert, R ^{[1
]}

Courchesne, G ^{[1
]}

机构：

[1] Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 44期

基金：

加拿大自然科学与工程研究理事会;

关键词：

alpha-tocotrienol; desymmetrization; lipase; asymmetric synthesis;

D O I：

10.1016/S0040-4039(02)01865-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-alpha-Tocotrienol was synthesized in 19% overall yield over six steps from this (S)-monoester. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7971 / 7973

页数：3

共 28 条

[1]

BOUZBOUZ S, 1994, SYNTHESIS-STUTTGART, P714

[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]

Danheiser R. L., 1993, ORG SYNTH, V71, P133

[4] CYSTOSEIROLS - NOVEL REARRANGED DITERPENOIDS OF MIXED BIOGENESIS FROM CYSTOSEIRACEAE (BROWN MARINE-ALGAE) [J].

FRANCISCO, C ;

BANAIGS, B ;

RAKBA, M ;

TESTE, J ;

CAVE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) :2707-2711

[5] Synthesis of various 2H-benzopyran compounds and their kinetic resolution by asymmetric hydrolysis of their racemic acetates mediated by lipases [J].

Goujon, JY ;

Zammattio, F ;

Kirschleger, B .

TETRAHEDRON-ASYMMETRY, 2000, 11 (11) :2409-2420

[6] ENANTIOSELECTIVE FUNCTIONALIZATION OF PROCHIRAL DIOLS VIA CHIRAL SPIROKETALS - PREPARATION OF OPTICALLY PURE 2-SUBSTITUTED 1,3-PROPANEDIOL DERIVATIVES AND ASYMMETRIC-SYNTHESIS OF CHROMAN RING AND SIDE-CHAIN OF ALPHA-TOCOPHEROL [J].

HARADA, T ;

HAYASHIYA, T ;

WADA, I ;

IWAAKE, N ;

OKU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (02) :527-532

[7] A kinetic resolution route to the (S)-chromanmethanol intermediate for synthesis of the natural tocols [J].

Hyatt, JA ;

Skelton, C .

TETRAHEDRON-ASYMMETRY, 1997, 8 (04) :523-526

[8] KINETIC RESOLUTION OF 2-SUBSTITUTED ESTERS CATALYZED BY A LIPASE EX PSEUDOMONAS-FLUORESCENS [J].

KALARITIS, P ;

REGENYE, RW ;

PARTRIDGE, JJ ;

COFFEN, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :812-815

[9]

KASPAREK S, 1980, VITAMIN E COMPREHENS, pCH2

[10] Vitamin E: Mechanisms of action as tumor cell growth inhibitors [J].

Kline, K ;

Yu, WP ;

Sanders, BG .

JOURNAL OF NUTRITION, 2001, 131 (01) :161S-163S

← 1 2 3 →