Model insect antifeedants. Synthesis of azadiradione fragments through acyl radicals cyclizations and stannane coupling reactions

A diastereoselective and versatile synthesis of the model insect antifeedant 16 related to azadiradione has been achieved in nine steps starting from α-cyclocitral 1. The key steps involve intramolecular alkene addition of an acyl radical and a Stille coupling reaction of a vinyl iodide with a stann...

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Bibliographic Details
Published in:Tetrahedron 1996-03, Vol.52 (13), p.4817-4828
Main Authors: Fernández-Mateos, Alfonso, Coca, Gustavo Pascual, Rubio González, Rosa, Tapia Hernández, Carolina
Format: Article
Language:English
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Summary:A diastereoselective and versatile synthesis of the model insect antifeedant 16 related to azadiradione has been achieved in nine steps starting from α-cyclocitral 1. The key steps involve intramolecular alkene addition of an acyl radical and a Stille coupling reaction of a vinyl iodide with a stannylfuran. A diastereoselective and versatile synthesis of the model insect antifeedant 16 related to azadiradione has been achieved in nine steps starting from α-cyclocitral 1. The key steps involve intramolecular alkene addition of an acyl radical and a Stille coupling reaction of a vinyl iodide with a stannylfuran.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00149-4