Indium mediated isoprenylation of carbonyl compounds with 2-bromomethyl-1,3-butadiene: a short synthesis of (±)-ipsenol

Abstract

Isoprenylation of aldehydes and ketones was directly performed by selective indium insertion on a mixture of 2-bromomethyl-1,3-butadiene and its vinylic isomers in good yields. A short synthesis of (±)-ipsenol, an aggregation pheromone of the Ips paraconfusus bark beetle, demonstrates the utility of this method in organic synthesis.

Keywords

• isoprenylation
• indium
• 2-bromomethyl-1,3-butadiene
• (±)-ipsenol