Synlett 1997; 1997(8): 1010-1012
DOI: 10.1055/s-1997-930
© 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.

The First Synthesis of a 10-Membered Ring by Olefin Metathesis: Jasmine Ketolactone

Alois Fürstner* , Thomas Müller
  • *Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany, Fax +49-(0)208-306-2980
Further Information

Publication History

Publication Date:
31 December 2000 (online)

An unprecedentedly short route to jasmine ketolactone (Z)-2 and its E-isomer is described, which is based on the efficient formation of the 10-membered ring via ring closing olefin metathesis (RCM) of diene 8. The latter is conveniently prepared by a three component coupling reaction consisting of the 1,4-addition of the lithium enolate of 3-butenyl (diphenylmethylsilyl)acetate 6 to 2-cyclopentenone and subsequent trapping of the enolate thus formed with allyl iodide.