Cyclohexadiene-trans-diols as versatile starting material in natural product synthesis: short and efficient synthesis of iso-crotepoxide and ent-senepoxide

A new synthesis of ent-senepoxide and iso-crotepoxide starting from microbially produced(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid via regio- and stereoselective epoxidation is described.

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2002-03 (5), p.494-495
Main Authors: Lorbach, Volker, Franke, Dirk, Nieger, Martin, Müller, Michael
Format: Article
Language:English
Subjects:
Biological Factors - chemical synthesis
Cyclohexanes - chemistry
Cyclohexanols - chemistry
Cyclohexenes
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Molecular Structure
Stereoisomerism
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Description
Summary:A new synthesis of ent-senepoxide and iso-crotepoxide starting from microbially produced(+)-trans-2,3-dihydroxy-2,3-dihydrobenzoic acid via regio- and stereoselective epoxidation is described.
ISSN:1359-7345
1364-548X
DOI:10.1039/b110420a