An approach to the total synthesis of welwistatin

Thomas J. Greshock; Raymond L. Funk

doi:10.1021/ol0608799

An approach to the total synthesis of welwistatin

Thomas J. Greshock, Raymond L. Funk

Chemistry

Research output: Contribution to journal › Article › peer-review

74 Scopus citations

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 6π 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.

Original language	English (US)
Pages (from-to)	2643-2645
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	12
DOIs	https://doi.org/10.1021/ol0608799
State	Published - Jun 8 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0608799

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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 6π 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.",

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AU - Funk, Raymond L.

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AB - 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 6π 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.

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JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

An approach to the total synthesis of welwistatin

Abstract

All Science Journal Classification (ASJC) codes

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