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

被引：14
作者：
Fraçkowiak, B
Ochalik, K
Bialonska, A
Ciunik, Z
Wawrzenczyk, C
Lochynski, S
机构：
[1] Wroclaw Univ Technol, Fac Chem, Dept Bioorgan Chem, PL-50370 Wroclaw, Poland
[2] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
[3] Univ Agr, Dept Chem, PL-50375 Wroclaw, Poland
来源：
TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 01期
关键词：
D O I：
10.1016/j.tetasy.2005.11.025
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
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 gamma-lactone group while the hydroxylactone 12 possesses a delta-lactone moiety situated trans to the gein-dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects. (c) 2005 Published by Elsevier Ltd.
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页码：124 / 129
页数：6
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