Enantioselective Total Synthesis of Multifidene, a Sex Pheromone of Brown Algae

Abstract

The total synthesis of multifidene, a sex pheromone found in brown algae, is described. The synthesis features the highly enantioselective and diastereoselective addition reaction of an aldehyde to a nitroolefin in the presence of a Hayashi–Jørgensen catalyst and a Nef reaction initiated by visible light irradiation. These key reactions enabled the 11-step synthesis from commercially available compounds. The synthetic pheromones are examined with gametes.

Keywords

• total synthesis
• sex pheromone
• multifidene
• conjugate addition
• Hayashi–Jørgensen catalyst
• Nef reaction