Oxycyclopropanes in organochemical synthesis. Total syntheses of (.+-.)-. alpha.-cuparenone and (.+-.)-. beta.-vetivone

E Wenkert, BL Buckwalter, AA Craveiro…

Index: Wenkert,E. et al. Journal of the American Chemical Society, 1978 , vol. 100, p. 1267 - 1273

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Citation Number: 82

Abstract

Abstract: A three-step, cyclopentenone synthesis scheme, involving the cyclopropanation of enol derivatives with diazomethyl ketones, the liberation of y-dicarbonyl compounds on acid hydrolysis of the resultant (3-oxycyclopropyl ketones, and intramolecular aldol condensation of the I, 4-diketo systems, is described. Its application to the synthesis of a prostanoid intermediate (5), a spiro [4S] decenone model (9), and an acorane intermediate (16) from ...