Download PDF
Synlett 2001; 2001(9): 1399-1402
DOI: 10.1055/s-2001-16777
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
28 August 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

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