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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 the cis-1,2-isoxazolidine. The oxidative cleavage of an all anti-triol with the excision of the central carbon is central to using ?-D-glucopyranoside as a traceless stereochemical template. This route furnishes a suitably protected synthon for the synthesis of zetekitoxin AB.

SUBMITTER: Paladugu SR

PROVIDER: S-EPMC4649947 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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

Paladugu Srinivas R SR Looper Ryan E RE

Tetrahedron letters 20151101 46

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 <i>cis</i>-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 th ...[more]

PMID: 26594065

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