Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma , and Their Enantiomers.

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.