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

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• 作者：Boż ; ena Frą ; ckowiak ; Katarzyna Ochalik ; Agata Biał ; oń ; ska ; Zbigniew Ciunik ; Czesł ; aw Wawrzeń ; czyk and Stanisł ; aw Lochyń ; ski
• 刊名：Tetrahedron ; Asymmetry
• 出版年：2006
• 期刊代码：108_09574166
• 类别：ch
• 出版时间：9 January 2006
• 卷：17
• 期：1
• 页码：124-129
• 文件大小：226 K

摘要

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.