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Synlett 1998; 1998(12): 1372-1374
DOI: 10.1055/s-1998-1962
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Synthesis of C-seco Limonoid Model Insect Antifeedants Related to Ochinolide

A. Fernández Mateos* , E. Martín de la Nava, G. Pascual Coca, A. Ramos Silvo, R. Rubio Gonzàlez
  • *Departamento de Química Orgánica. Facultad de C. Químicas. Universidad de Salamanca. Salamanca. Spain; E-mail: afmateos@gugu.usal.es
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Publication History

Publication Date:
31 December 2000 (online)

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A short and selective synthesis of C-seco limonoid model insect antifeedant related to ochinolide was accomplished in seven steps from α-cyclocitral. The key steps are the electrocyclization of a β-acyl divinyl ketone induced by perchloric acid, and a selective retroclaisen reaction. A rare example of atropisomerism was found in the trisubstituted cyclopentenone 6 key intermediate.

Nazarov reaction - retroclaisen reaction - perchloric acid - antifeedant - limonoids