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Synlett 1995; 1995(5): 409-410
DOI: 10.1055/s-1995-4989
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A New Route to Model Insect Antifeedants Related to Azadiradione Via Cationic Electrocyclization

A. Fernández Mateos* , A. Lopéz Barba, G. Pascual Coca, R. Rubio González, C. Tapia Hernández
  • *Departamento de Química Orgánica. Facultad de C. Químicas. Universidad de Salamanca. Salamanca. Spain
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Publication History

Publication Date:
31 December 2000 (online)

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Starting from citral, a concise and efficient synthesis of the model insect antifeedant 9 based on the C, D and E rings of the limonoid azadiradione has been achieved. The key step involves a selective and unusual Nazarov cyclization of 4 to close the five-membered ring thus to assemble the carbon framework, followed by Lewis acid-induced dyotropic rearrangement of the epoxide 7 to set the required alpha-furan stereochemistry in the target compound.

Synthesis - antifeedant - limonoids - azadiradione - cationic electrocylization