Concise syntheses of iridodial and actinidine

CHED 542

Joel S. Beckett, beckettj@kenyon.edu and John Hofferberth, hofferberthj@kenyon.edu. Department of Chemistry, Kenyon College, Gambier, OH 43022
The concise syntheses of two known insect semiochemicals thought to be involved in the myrmecophilic relationship between butterflies of the Lycanidae family and ants of genus Iridomyrmex have been developed. Iridodial was prepared in four synthetic steps from commercial citronellal utilizing an intramolecular hetero 4 + 2 cycloaddition in the key step. Additionally, both enantiomers of actinidine have been prepared in two steps from enantiomercially enriched citronellal using a novel bicyclic pyridine synthesis.