Triquinane sesquiterpenes. An iterative, highly stereocontrolled synthesis of (.+-.)-silphinene

LA Paquette, A Leone-Bay

Index: Paquette,L.A.; Leone-Bay,A. Journal of the American Chemical Society, 1983 , vol. 105, p. 7352

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Citation Number: 50

Abstract

Abstract: A total synthesis of (&)-silphinene, a tricyclopentanoid sesquiterpene isolated from the roots of Silphium perfoliatum L., has been achieved. This structurally interesting triquinane was constructed in 15 steps and isolated in efficient overall yield. The key element of the synthesis was the implementation of an iterative cyclopentannulation scheme consisting of twofold conjugate addition of a functionalized organocopper reagent and ...