Stereochemistry of terpene derivatives. Part 5: Synthesis of chiral lactones fused to a carane system - Insect feeding deterrents

Article abstract of DOI:10.1016/j.tetasy.2005.11.025

Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a γ-lactone group while the hydroxylactone 12 possesses a δ-lactone moiety situated trans to the gem- dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects.