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

M Morita, N Mase, H Yoda, K Takabe

Index: Morita, Motoaki; Mase, Nobuyuki; Yoda, Hidemi; Takabe, Kunihiko Tetrahedron Asymmetry, 2005 , vol. 16, # 19 p. 3176 - 3182

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Citation Number: 20

Abstract

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.