Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene

Beilstein J Org Chem. 2016 Jul 1:12:1361-5. doi: 10.3762/bjoc.12.129. eCollection 2016.

Abstract

The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the product bromochloride is demonstrated by the first total synthesis of an antibacterial polyhalogenated monoterpene, (-)-anverene.

Keywords: enantioselective catalysis; halogenation; natural products; total synthesis.