Total synthesis of the paniculides

AB Smith III, RE Richmond

Index: Smith III; Richmond Journal of the American Chemical Society, 1983 , vol. 105, # 3 p. 575 - 585

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Citation Number: 48

Abstract

Abstract: In this, a full account, we disclose the first total synthesis of paniculides AC (1-3), three highly oxygenated sesquiterpenes isolated in 1968 by Overton et al. from hypocotyl and stem tissue cultures of Andrographis paniculata. Our approach, which is both highly efficient and stereocontrolled and furthermore serves to confirm for thefirst rime the structural assignments of the paniculides, begins with the facile photochemical [2+ 21 cycloaddition ...