Synthesis of 8-epi-Dendrobine

RF Borch, AJ Evans, JJ Wade

Index: Borch; Evans; Wade Journal of the American Chemical Society, 1977 , vol. 99, # 5 p. 1612 - 1619

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Citation Number: 39

Abstract

Abstract: The synthesis of 8-epi-dendrobine (lb) is described in which stereochemistry is established via intramolecular Diels-Alder cyclization of triene ester 2 to give the unsaturated nitrile ester 3. Intermediate 3 is elaborated to lb via two independent synthetic routes, one proceeding via. keto lactone 12d and the other via amino ester 14. Inversion of stereochemistry at C-8 is believed to occur as a consequence of diene isomerization ...