A new bromo trienyne: synthesis of all-E, conjugated tetra-, penta-, and hexaenes common to oxo polyene macrolide antibiotics

BH Lipshutz, B Ullman, C Lindsley…

Index: Lipshutz; Ullman; Lindsley; Pecchi; Buzard; Dickson Journal of Organic Chemistry, 1998 , vol. 63, # 18 p. 6092 - 6093

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Citation Number: 42

Abstract

In a recent report from these laboratories, 1 a new “linchpin” 1 was disclosed that allows for rapid construction of the all-E oxopolyene network characteristic of many polyene macrolide antifungal agents (Figure 1). 2 This methodology relies on an initial Pd (0) coupling, where 1 serves as the nucleophilic partner. The acetylenic terminus can be regioand stereoselectively hydrozirconated, and while introduction of an acyl moiety could be ...