METHYL (3R)-3-HYDROXYHEX-5-ENOATE AS A PRECURSOR TO CHIRAL MEVINIC ACID ANALOGS

被引：47
作者：
BENNETT, F
KNIGHT, DW
FENTON, G
机构：
[1] UNIV NOTTINGHAM,DEPT CHEM,UNIV PK,NOTTINGHAM NG7 2RD,ENGLAND
[2] RHONE POULENC LTD,DAGENHAM,ESSEX,ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 01期
关键词：
D O I：
10.1039/p19910000133
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Baker's yeast reduction of methyl 3-oxohex-5-enoate 14b provides methyl (3R)-3-hydroxyhex-5-enoate 15b with 78% enantiomeric enrichment. Subsequent seleno- and iodo-lactonization of derived hex-5-enoic acids leads to valerolactones 18, 19, 25 and 26 which are suitable for the subsequent elaboration of a variety of mevinic acid analogues. The absolute configuration of the major enantiomer produced in the initial yeast reduction was determined by correlation with natural (S)-(+)-parasorbic acid 23.
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页码：133 / 140
页数：8
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