Semester

Fall

Date of Graduation

2013

Document Type

Dissertation

Degree Type

PhD

College

Eberly College of Arts and Sciences

Department

Chemistry

Committtee 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.

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