132697-51-9Relevant academic research and scientific papers
CHIRAL SYNTHONS FOR THE ELABORATION OF MEVINIC ACID ANALOGUES
Bennett, Frank,Kinght, David W.,Fenton, Garry
, p. 4865 - 4868 (1988)
Baker's yeast reduction of methyl 3-oxo-5-hexenoate (6b) affords the (R)-hydroxy-ester (7b) (76percent ee) wich is converted into the lactones (15) and epoxy-ester (19), synthons of the lactone part of the mevinic acids.
Methyl (3R)-3-Hydroxyhex-5-enoate as a Precursor to Chiral Mevinic Acid Analogues
Bennett, Frank,Knight, David W.,Fenton, Garry
, p. 133 - 140 (2007/10/02)
Baker's yeast reduction of methyl 3-oxohex-5-enoate 14b provides methyl (3R)-3-hydroxyhex-5-enoate 15b with 78percent 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.
