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Tetrahedron Lett. 2015 Nov 18;56(46):6332-6334.

Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB.

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1
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112.

Abstract

A synthesis of the 1,2-isoxazolidine fragment of the potent voltage gated sodium channel blocker, zetekitoxin AB is described. The synthesis utilizes an intramolecular nitrone -olefin 1,3-dipolar cycloaddition to establish the stereochemistry of the cis-1,2-isoxazolidine. The oxidative cleavage of an all anti-triol with the excision of the central carbon is central to using α-D-glucopyranoside as a traceless stereochemical template. This route furnishes a suitably protected synthon for the synthesis of zetekitoxin AB.

KEYWORDS:

1,2-isoxazolidine; Zetikitoxin AB; dipolar cycloaddition; nitrone; saxitoxin

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