Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, <i>Lyclene dharma dharma</i>, and Their Enantiomers

Abstract

The Lichen moth, Lyclene dharma dharma (Arctiidae, Lithosiinae), plays a significant role in forest ecosystem dynamics. A concise and novel method to synthesize the active sex pheromone components, (S)-14-methyloctadecan-2-one ((S)-1), (S)-6-methyloctadecan-2-one ((S)-2), and their enantiomers has been developed. Key steps in the synthesis include the use of Evans’ chiral auxiliaries, Grignard cross-coupling reactions, hydroboration–oxidation, and Wacker oxidation. The synthesized sex pheromone components hold potential value for studies on communication mechanisms, species identification, and ecological management.

Keywords

• sex pheromone
• <i>Lyclene dharma dharma</i>
• Evans’ chiral auxiliary
• enantioselective synthesis