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

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