title: Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB.
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 thecis-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.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112.
authors.forename: Srinivas R
authors.initials: SR
authors.lastname: Paladugu
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, UT 84112.
authors.forename: Ryan E
authors.initials: RE
authors.lastname: Looper
keywords: 1,2-isoxazolidine; Zetikitoxin AB; dipolar cycloaddition; nitrone; saxitoxin