Biorational synthesis of iridomyrmecin diastereomers from catnip oil

Abstract 4 S ,4a S ,7 S ,7a R ; 4 R ,4a S ,7 S ,7a R ; 4 S ,4a S ,7 S ,7a S , and 4 R ,4a S ,7 S ,7a S diastereomers of iridomyrmecin have been prepared in 5 steps from 4a S ,7 S ,7a R and 4a S ,7 S ,7a S -nepetalactones, major components of catnip oil. 4 S ,4a S ,7 S ,7a R and 4 R ,4a S ,7 S ,7a R -iridomyrmecin have been identified as defensive compounds from Iridomyrmex ants.