Tandem 1, 3-dipolar cycloaddition and electrophilic cyclization reactions: cyclic ether subunits of polyether antibiotics from unsaturated isoxazolines

…, MM Olmstead, MJ Rodriguez

Index: Kurth, Mark J.; Rodriguez, Michael J.; Olmstead, Marilyn M. Journal of Organic Chemistry, 1990 , vol. 55, # 1 p. 283 - 288

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Citation Number: 37

Abstract

A new strategy for the construction of polyether antibiotic substructural units [spiroketals (I), tetrahydrofurans (111, and tetrahydropyrans (III)] consisting of bis-addition of an oxygen nucleophile across an a, w-diene moiety (ie, IV) is described. The method exploits a tandem 1, 3-dipolar cycloaddition/electrophilic cyclization sequence that proceeds via the intermediacy of an isoxazoline. Experiments presented illustrate the versatility of this ...