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The First Synthesis of a 10-Membered Ring by Olefin Metathesis: Jasmine Ketolactone
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.
ring closing metathesis - medium sized rings - decanolides - three component coupling - 1,4-addition