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

Article abstract of DOI:10.1055/s-1997-930

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.