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

Alois Fürstner; Thomas Müller

doi:10.1055/s-1997-930

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

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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

Abstract

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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.

ring closing metathesis - medium sized rings - decanolides - three component coupling - 1,4-addition

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