5-METHOXY-PENTONO-1,4-LACTONES FROM (R)-2-HYDROXY-5-METHOXY-3-PENTENOIC ACID OBTAINED BY BIOREDUCTION OF THE 2-OXO ACID

被引：14

作者：

BONNAFFE, D ^{[1
]}

SIMON, H ^{[1
]}

机构：

[1] TECH UNIV MUNICH,LEHRSTUHL ORGAN CHEM & BIOCHEM,LICHTENBERGSTR 4,W-8046 GARCHING,GERMANY

来源：

TETRAHEDRON | 1992年 / 48卷 / 44期

关键词：

D O I：

10.1016/S0040-4020(01)81186-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various 5-methoxy-pentono-1,4-lactones and derivates thereof were synthesised from propargyl alcohol or its methyl ether. The key step was the enantioselective reduction of 2-oxo-5-alkoxy-3-pentenoic acids by resting cells of Proteus vulgaris. The (R)-2-hydroxy-5-methoxy-3-pentenoic acid (ee. > 96%) was further functionalized via epoxidation, or hydroxylation with osmium tetroxide, or bromine addition, with modest to good diastereoselectivity, leading to 5-methoxy-pentono-1,4-lactones of the series (L)-arabino, (D)-ribo, (L)-lyxo, and (D)-xylo. A new way to obtain 2-oxo-3-enoic acids is described, using Pd mediated cross coupling between vinyl tin compounds and oxalyl chloride monoesters.

引用

页码：9695 / 9706

页数：12

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