Total Synthesis of (.+-.)-Atpenin B. An Original" Clockwise" Functionalization of 2-Chloropyridine

…, M Mallet, O Mongin, G Queguiner

Index: Trecourt, Francois; Mallet, Marc; Mongin, Olivier; Queguiner, Guy Journal of Organic Chemistry, 1994 , vol. 59, # 21 p. 6173 - 6178

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Citation Number: 39

Abstract

This molecule, which exhibits a pentasubstituted pyridine structure, was prepared from 2- chloropyridine in 13 steps, by metalating and then functionalizing, one after another, all the remaining positions of the pyridine ring. The methodology involves four metalation steps (including metalation of 2, 3-dimethoxypyridine and pyridyl Nfl-diisopropylcarbamates), one halogen-scrambling step, and one bromine-lithium exchange step.