Nicholas reactions with carboxylic acids for the synthesis of macrocyclic diolides

KM Shea, KD Closser, MM Quintal

Index: Shea, Kevin M.; Closser, Kristina D.; Quintal, Miriam M. Journal of Organic Chemistry, 2005 , vol. 70, # 22 p. 9088 - 9091

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Citation Number: 9

Abstract

We have developed a new strategy for the preparation of diolides using a cascade of Nicholas reactions. The carboxylic acid nucleophiles in these reactions are virtually unstudied participants in transformations of this type. Using this methodology, a 16- membered cobalt-complexed cyclic diyne is available in 28% yield over eight steps (an average of 85% per step). We can also easily access the uncomplexed diolide in one ...