Methyl (3R)-3-hydroxyhex-5-enoate as a precursor to chiral mevinic acid analogues

doi:10.1039/P19910000133

Paper

DOI: 10.1039/P19910000133

Methyl (3R)-3-hydroxyhex-5-enoate as a precursor to chiral mevinic acid analogues

Published 1991 · F. Bennett, D. Knight, G. Fenton

Journal of The Chemical Society-perkin Transactions 1

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Abstract

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.

Study Snapshot

Yeast reduction of methyl 3-oxohex-5-enoate leads to enantiomeric enrichment of 78%, which can be used to create various mevinic acid analogues.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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