The Journal of Organic Chemistry

A new and efficient approach to macrocyclic keto lactones

MR Karim, P Sampson

Index: Karim, Mohammad R.; Sampson, Paul Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 598 - 605

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Citation Number: 20

Abstract

A new and efficient method for macrolactonization has been developed. The intramolecular nucleophilic displacement of chloride from the highly electrophilic a-chloro ketone moiety in 15 by a remote carboxylate nucleophile resulted in the clean formation of the 11-membered keto lactone 1. Relatively high substrate concentrations (up to 18 mM) could be employed without formation of dimeric or oligomeric byproducts. The slow mixing of substrate and ...