Synthesis of (3R)- and (3S)-fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids: The (3R)- and (3S)-fluoro analogues of (-)-shikimic acid

被引：16

作者：

Brettle, R

Cross, R

Frederickson, M

Haslam, E

MacBeath, FS

Davies, GM

机构：

[1] UNIV SHEFFIELD,DEPT CHEM,SHEFFIELD S3 7HF,S YORKSHIRE,ENGLAND

[2] ZENECA PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 11期

关键词：

D O I：

10.1016/0960-894X(96)00215-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

(3R)-and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3R)-and (3S)-fluoro analogues of (-)-shikimic acid) have been synthesised from (-)-shikimic acid via an intermediate epoxide (a fungal metabolite from Chalara microspora) that underwent acid catalysed hydrolysis to afford the first stereospecific synthesis of (-)-3-epi-shikimic acid. Copyright (C) 1996 Elsevier Science Ltd

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页码：1275 / 1278

页数：4

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