A Stereoselective Synthesis of (±)-C-Secolimonoid BCDE Model Compounds Related to the Insect Antifeedant Ohchinolide

A short and stereoselective synthesis of a (±)-BCDE C-secolimonid model insect antifeedant related to ohchinolide and nimbolidin was accomplished in 13 (30% overall yield) and 15 (30% overall yield) steps, respectively, from ethyl drimanate. The key steps are the torquoselective electrocyclization o...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-11, Vol.66 (23), p.7632-7638
Main Authors: Mateos, Alfonso Fernández, Martín de la Nava, Eva M, González, Rosa Rubio
Format: Article
Language:English
Subjects:
Animals
Cyclopropanes - chemical synthesis
Feeding Behavior - drug effects
Insecta - drug effects
Insecticides - chemical synthesis
Insecticides - pharmacology
Larva - drug effects
Plants
Pyrans - chemical synthesis
Spodoptera - drug effects
Stereoisomerism
Triterpenes - chemical synthesis
Triterpenes - chemistry
Triterpenes - pharmacology
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Summary:A short and stereoselective synthesis of a (±)-BCDE C-secolimonid model insect antifeedant related to ohchinolide and nimbolidin was accomplished in 13 (30% overall yield) and 15 (30% overall yield) steps, respectively, from ethyl drimanate. The key steps are the torquoselective electrocyclization of the divinyl ketone 6, induced by perchloric acid, and the stereoselective rearrangement of the hydroxy lactone 12, inspired in a biosynthetic proposal. An alternative route, which provides access to (±)-BCDE ohchinolide and nimbolidin isomers, is also described.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo010449q