Total synthesis of (+)-hydroxyjatrophone A and (+)-hydroxyjatrophone B

AB Smith III, AT Lupo Jr, M Ohba…

Index: Smith, Amos B.; Lupo, Andrew T.; Ohba, Masashi; Chen, Kwunmin Journal of the American Chemical Society, 1989 , vol. 111, # 17 p. 6648 - 6656

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Citation Number: 43

Abstract

Abstract: A full account of the first total synthesis of (+)-hydroxyjatrophone A (2) and (+)- hydroxyjatrophone B (3), two antileukemic diterpene macrocycles isolated from Jatropha gossypiifolia, is presented. Central to the synthetic strategy was an intramolecular Mukaiyama acetal-aldol reaction that generated the 1 1-membered ring. Of paramount interest with respect to the hydroxyjatrophones was the compatibility of the highly sensitive ...