The First Synthesis of a 10-Membered Ring by Olefin Metathesis: Jasmine Ketolactone
- 1 August 1997
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1997 (8) , 1010-1012
- https://doi.org/10.1055/s-1997-930
Abstract
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.Keywords
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