Methyl (3R)-3-hydroxyhex-5-enoate as a precursor to chiral mevinic acid analogues
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 133-140
- https://doi.org/10.1039/p19910000133
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.Keywords
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