Total synthesis of (-)-and ent-(+)-vindoline and related alkaloids

H Ishikawa, GI Elliott, J Velcicky, Y Choi…

Index: Ishikawa, Hayato; Elliott, Gregory I.; Velcicky, Juraj; Choi, Younggi; Boger, Dale L. Journal of the American Chemical Society, 2006 , vol. 128, # 32 p. 10596 - 10612

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Citation Number: 110

Abstract

A concise 11-step total synthesis of (-)-and ent-(+)-vindoline (3) is detailed based on a unique tandem intramolecular [4+ 2]/[3+ 2] cycloaddition cascade of a 1, 3, 4-oxadiazole inspired by the natural product structure, in which three rings and four CC bonds are formed central to the characteristic pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. As ...