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An approach to the total synthesis of welwistatin.

ABSTRACT: An approach to the total synthesis of the antimicrotubule agent welwistatin is described. Key transformations include (1) a 7-endo intramolecular conjugate addition reaction of enone 6 to deliver the strained bicyclo[4.3.1]decanone 5; (2) a 6pi electrocyclic ring closure of trienecarbamate 16 followed by oxidation to afford protected aniline 17; and (3) an intramolecular cyclization of acetic acid derivative 18 to give rise to indole 19. [reaction: see text]

SUBMITTER: Greshock TJ

PROVIDER: S-EPMC2547338 | biostudies-literature | 2006 Jun

REPOSITORIES: biostudies-literature

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An approach to the total synthesis of welwistatin.

Greshock Thomas J TJ Funk Raymond L RL

Organic letters 20060601 12

An approach to the total synthesis of the antimicrotubule agent welwistatin is described. Key transformations include (1) a 7-endo intramolecular conjugate addition reaction of enone 6 to deliver the strained bicyclo[4.3.1]decanone 5; (2) a 6pi electrocyclic ring closure of trienecarbamate 16 followed by oxidation to afford protected aniline 17; and (3) an intramolecular cyclization of acetic acid derivative 18 to give rise to indole 19. [reaction: see text] ...[more]

PMID: 16737334

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