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Synlett 2001; 2001(9): 1399-1402
DOI: 10.1055/s-2001-16777
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A Biomimetic Approach to C-secolimonoids: Synthesis of CDE Ohchinolide and Nimbolidin Model Compounds

A. Fernández Mateos* , E. Martín de la Nava, R. Rubio González
  • *Departamento de Química Orgánica, Facultad de C. Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008-Salamanca, Spain; Fax + 34 923 294574; E-mail: afmateos@gugu.usal.es
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Publication Date:
28 August 2001 (online)

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A concise and stereoselective synthesis of CDE ohchinolide and nimbolidin model compounds has been accomplished in ten and twelve steps respectively from α-cyclocitral, in 30% overall yield. The key step is a biomimetic type of allylic rearrangement induced by thionyl chloride. A potent insect antifeedant activity was found for two of the model compounds snythesised.

stereoselective synthesis - allylic rearrangement - C-secolimonoids - ohchinolide - nimbolidin

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