Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid

被引：40

作者：

Ermolenko, L ^{[1
]}

Sasaki, NA ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 02期

关键词：

D O I：

10.1021/jo0521192

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These alpha-hydroxy esters were transformed into four gamma-alkoxy-alpha,beta-unsaturated esters C via the intermediates B and subsequent Wittig olefination reactions. Each one of compounds C was subjected to dihydroxylation to provide a set of two diols D. Anti/lsyn-differentiation in diol formation was manipulated by using (DHQD)(2)PHAL and (DHQ)(2)PHAL as chiral ligands. Further two-step reaction sequence affords all eight diastereopure L-hexoses.

引用

页码：693 / 703

页数：11

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