Palladium-catalyzed syntheses of indoles, pyrroloindoles, quinolines; a base-mediated formation of N-alkoxyindoles, and progress toward the first total synthesis of Echinosulfone A.

Author

Serge R. Banini

Date of Graduation

2008

Document Type

Dissertation

Degree Type

PhD

College

Eberly College of Arts and Sciences

Department

Chemistry

Committee Chair

Björn C. G. Söderberg

Committee Member

Peter M. Gannett

Committee Member

George A. O’Doherty

Committee Member

John H. Penn

Committee Member

Jeffrey L. Petersen

Abstract

A variety of heterocyclic compounds including indoles, quinolines, and pyrroloindoles has been synthesized. The key step in these alkaloids' syntheses is a palladium-catalyzed reductive N-heteroannulation previously discovered in our laboratory. The ultimate reducing agent in these palladium-catalyzed cyclizations is carbon monoxide. Furthermore, a base-mediated formation of 2-unsubstituted N-alkoxyindoles is described from readily available nitrostyrenes. Finally, progress towards the first total synthesis of the highly bioactive Echinosulfone A is reported.

Recommended Citation

Banini, Serge R., "Palladium-catalyzed syntheses of indoles, pyrroloindoles, quinolines; a base-mediated formation of N-alkoxyindoles, and progress toward the first total synthesis of Echinosulfone A." (2008). Graduate Theses, Dissertations, and Problem Reports. 8440.
https://researchrepository.wvu.edu/etd/8440