APPLICATION OF OLEFIN METATHESIS TO ORGANIC SYNTHESIS. SYNTHESES OF CIVETONE AND MACROLIDES

Article abstract of DOI:10.1016/0040-4039(80)88007-5

Diethyl 9-octadecene-1,18-dioate was obtained in 87percent yield based on 50percent theoretical conversion by the olefin metathesis reaction catalyzed by WOCl4-Cp2TiMe2.The Dieckmann condensation of this diester using potassium hydride afforded 2-ethoxycarbonylcyclo-9-heptadecenone, which was converted by hydrolysis and decarboxylation to cyclo-9-heptadecenone (civetone) as a mixture of cis and trans isomers (1.3 : 1) in 54percent yield.Also 9-octadecen-18-olide was obtained in 17.9percent by the metathesis of oleyl oleate.