Lactones. Part 15: Synthesis of chiral spirolactones with a carane system—insect feeding deterrents

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-unsat...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 13; no. 16; pp. 1761 - 1767
Main Authors Lochyński, Stanisław, Frąckowiak, Bożena, Olejniczak, Teresa, Ciunik, Zbigniew, Wawrzeńczyk, Czesław
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.08.2002
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
TERPENOID LACTONES
ANTIFEEDANTS
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Summary: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. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(02)00476-7