A simplified synthesis of (R)-(−)-muscone using a ring-opening reaction of (R)-(+)-β-methyl-β-propiolactone

A chiral macrocyclic precursor can be constructed via a ring-opening reaction of (R)-(+)-β-methyl-β-propiolactone with a functionalized organocuprate with no loss of enantiomeric excess. The carboxylic acid precursor was used as a chiral building block for the synthesis of chiral muscone and musky macrolactones.

Graphical abstractChiral (R)-muscone was constructed via ring-opening reaction of (R)-(+)-β-methyl-β-propiolactone with functionalized organocuprate with almost no loss of optical purity.Figure optionsDownload full-size imageDownload as PowerPoint slide

(3R,16Z)-3-Methylpentacos-16-enoic acidC26H50O2Ee = 93%[α]D25=+3.2 (c 1.1, CHCl3)