121772-47-2

Upstream product

• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 
• 119003-49-5 (3R)-(-)-3-hydroxyhex-5-enoic acid 
• 100636-39-3 methyl 3-carbonyl-5-hexenoate 
• 121772-46-1 (3R)-3-hex-5-enoic acid 

Relevant academic research and scientific papers

Methyl (3R)-3-Hydroxyhex-5-enoate as a Precursor to Chiral Mevinic Acid Analogues

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.

CHIRAL SYNTHONS FOR THE ELABORATION OF MEVINIC ACID ANALOGUES

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.