Semester
Fall
Date of Graduation
2018
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Björn C. G. Söderberg
Committee Co-Chair
Jeffrey L. Petersen
Committee Member
Jeffrey L. Petersen
Committee Member
Kung K. Wang
Committee Member
Brian V. Popp
Committee Member
Patrick Callery
Abstract
The Watanabe-Cenini-Söderberg reductive N-heterocyclization has emerged as a powerful tool for the synthesis of a variety of functionalized indoles. Söderberg’s elaboration of this methodology has been utilized as a late-stage cyclization protocol for the synthesis of azepinoindole alkaloids, a class of natural products characterized by an azepane skeleton fused with an indole ring. Short syntheses of the naturally occurring azepino[5,4,3-cd]indole alkaloids, cimitrypazepine, fargesine, and the diastereomeric hyrtioreticulins C & D have been completed starting from commercially available tetra-substituted benzene derivatives. The key azepinoindole core in each case was assembled via an intramolecular Mizoroki-Heck reaction followed by a Watanabe-Cenini-Söderberg reductive N-heterocyclization. Synthesis of aurantioclavine using a similar strategy is currently underway.
Recommended Citation
Ghimire, Ganesh, "Syntheses of azepinoindole alkaloids cimitrypazepine, fargesine and hyrtioreticulins C & D" (2018). Graduate Theses, Dissertations, and Problem Reports. 3745.
https://researchrepository.wvu.edu/etd/3745