SYNTHESIS OF LUORO-(4R,5R)-DIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC AND LUORO-(4R,5R)-DIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACIDS - THE (3R)-FLUORO AND (3S)-FLUORO ANALOGS OF (-)-SHIKIMIC ACID

Authors
BRETTLE R CROSS R FREDERICKSON M HASLAM E MACBEATH FS DAVIES GM
Citation
R. Brettle et al., SYNTHESIS OF LUORO-(4R,5R)-DIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC AND LUORO-(4R,5R)-DIHYDROXY-1-CYCLOHEXENE-1-CARBOXYLIC ACIDS - THE (3R)-FLUORO AND (3S)-FLUORO ANALOGS OF (-)-SHIKIMIC ACID, Bioorganic & medicinal chemistry letters, 6(11), 1996, pp. 1275-1278
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
6
Issue
11
Year of publication
1996
Pages
1275 - 1278
Database
ISI
SICI code
0960-894X(1996)6:11<1275:SOLAL>2.0.ZU;2-7
Abstract
(3R)-and luoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3R)-and (3S)-fluoro analogues of (-)-shikimic acid) have been synthe sised from (-)-shikimic acid via an intermediate epoxide (a fungal met abolite from Chalara microspora) that underwent acid catalysed hydroly sis to afford the first stereospecific synthesis of (-)-3-epi-shikimic acid. Copyright (C) 1996 Elsevier Science Ltd