Total synthesis of (+)-β-himachalene

Abstract

An enantioselective synthesis of (+)-β-himachalene (2) was accomplished starting from (1S,2R)-1,2-epoxy-p-menth-8-ene (3) in 15 or 16 steps with an overall yield of ca. 6% (Schemes 3, 5, and 6). Key transformations include an Ireland-Claisen rearrangement, a Corey oxidative cyclization, and a ring expansion. © 2006 Verlag Helvetica Chimica Acta AG.