Novel sequential sigmatropic rearrangements of allylic diols: application to the total synthesis of (−)-kainic acid

K Kitamoto, M Sampei, Y Nakayama, T Sato…

Index: Kitamoto, Katsunori; Sampei, Mana; Nakayama, Yasuaki; Sato, Takaaki; Chida, Noritaka Organic Letters, 2010 ,  vol. 12,  # 24  p. 5756 - 5759

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Citation Number: 28

Abstract

Sequential sigmatropic rearrangements (Claisen/Claisen and Claisen/Overman) of enantiopure allylic diols are described. The reactions proceeded in complete diastereoselectivity without protecting group manipulations. The sequential Claisen/Overman rearrangement was successfully applied to the total synthesis of (−)-kainic acid.