6533b862fe1ef96bd12c6242

RESEARCH PRODUCT

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

Agata BiałońskaCzesław WawrzeńczykKatarzyna OchalikBożena Frąckowiak-wojtasekStanisław LochyńskiZbigniew Ciunik

subject

Inorganic ChemistryTerpeneChemistryStereochemistryOrganic ChemistryDiastereomerMoietyOrganic chemistryPhysical and Theoretical ChemistryRing (chemistry)CatalysisStereocenter

description

Abstract 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.

yearjournalcountryeditionlanguage
2006-01-01Tetrahedron-Asymmetry
10.1016/j.tetasy.2005.11.025https://doi.org/10.1016/j.tetasy.2005.11.025