Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core

Richard W Heidebrecht Jr; Brian Gulledge; Stephen F Martin

doi:10.1021/ol1006373

Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core

Org Lett. 2010 Jun 4;12(11):2492-5. doi: 10.1021/ol1006373.

Authors

Richard W Heidebrecht Jr¹, Brian Gulledge, Stephen F Martin

Affiliation

¹ Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.

Abstract

The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyanobacteria / chemistry
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure

Substances

Indole Alkaloids
N-methylwelwitindolinone C isothiocyanate

Abstract

Publication types

MeSH terms

Substances

Grants and funding