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/Thesis

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