0000000000828271
AUTHOR
Teresa Olejniczak
Stereochemistry of terpene derivatives. Part 4:☆ Fragrant terpenoid derivatives with an unsaturated gem-dimethylbicyclo[3.1.0]hexane system
Abstract Starting from (+)-3-carene 1 several chiral fragrant compounds with the bicyclo[3.1.0]hexane system 4–6 and 10–20 were synthesized. These compounds are structural analogues of naturally occurring fragrant compounds, such as ionones and damascones, and possess either an endo- or an exo-cyclic double bond in the bicyclo[3.1.0]hexane moiety. The absolute configuration of selected products was confirmed by X-ray crystallography and circular dichroism analysis.
Lactones. Part 15: Synthesis of chiral spirolactones with a carane system—insect feeding deterrents
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.