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

Taiki Umezawa, Misaki Hara, Nana Kinoshita-Terauchi, Fuyuhiko Matsuda

Organics · pp. 187–195 · Published 8 Jul 2022

10.3390/org3030015

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.

Enantioselective synthesis Sex pheromone Pheromone Aldehyde Total synthesis Brown algae Catalysis Algae

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