Semester
Fall
Date of Graduation
2013
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Bjorn C. G. Soderberg
Committee Co-Chair
Robert K. Griffith
Committee Member
John H. Penn
Committee Member
Jeffrey L. Petersen
Committee Member
Kung K. Wang
Abstract
Palladium-catalyzed reductive N-heteroannulation of ortho-nitrostyrenes has become a synthetically useful method for the construction of indoles and indole-based heterocycles. Soderberg's elaboration of this methodology has been utilized in the synthesis of indoles and quinolines from a common precursor. The same protocol has also been employed in the synthesis of the indole alkaloid Salviadione. A systematic investigation of chemoselectivity in Kosugi-Migita-Stille coupling reactions provided the basis for the synthesis of isomeric pyrroloindoles through palladium-catalyzed reductive double N-heteroannulation of dinitro-dialkenyl benzenes.
Recommended Citation
Cummings, Matthew Marshall, "A base modulated synthesis of indoles and quinolines, an expedient synthesis of salviadione, and chemoselective couplings en route to indoles and pyrroloindoles" (2013). Graduate Theses, Dissertations, and Problem Reports. 388.
https://researchrepository.wvu.edu/etd/388
