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RESEARCH PRODUCT
Lactones. Part 15: Synthesis of chiral spirolactones with a carane system—insect feeding deterrents
Zbigniew CiunikCzesław WawrzeńczykStanisław LochyńskiBożena Frąckowiak-wojtasekTeresa Olejniczaksubject
Inorganic Chemistrychemistry.chemical_compoundChemistryOrganic ChemistryIodolactonizationDehydrohalogenationHalogenationOrganic chemistryTributyltin hydridePhysical and Theoretical ChemistrySpectral dataCatalysisdescription
Abstract Starting from (+)-3-carene 1 several spirolactones with carane backbone were synthesized. δ-Hydroxy-γ-lactone 5 was obtained by acidic lactonization of a γ,δ-epoxy ester. Iodolactone 8 and bromolactone 9 were products of iodolactonization of γ,δ-unsaturated acid 7 and bromolactonization of γ,δ-unsaturated ester 3 respectively. The halo lactones were subjected to reductive dehalogenation with tributyltin hydride and dehydrohalogenation with DBU. The structures of the lactones obtained were confirmed by X-ray analysis and spectral data.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-08-01 | Tetrahedron-Asymmetry |