Degree Type

Dissertation

Date of Award

1991

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

George A. Kraus

Abstract

The Diels-Alder reaction has been known to organic chemists for several decades. This reaction, as well as its intramolecular version, has been utilized and studied extensively by both synthetic and physical organic chemists. This study was undertaken to determine the potential of the indole nucleus to participate in an intramolecular Diels-Alder reaction, to study the make-up of the tether that joins the diene and the dienophile and to apply what was discovered to a synthesis of a natural product;Thermolysis of several N-substituted indoles gave cyclized products. It was determined that an amide or an urea moiety could make-up the tether. However, when a carbamate was employed, no reaction occurred;A successful case of an amide as part of the tether was expanded in an attempted synthesis of strychnine. Strychnine is a heptacyclic natural product. We have synthesized several hexacyclic intermediates in our approaches to this natural product.

DOI

https://doi.org/10.31274/rtd-180813-9430

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/

Copyright Owner

Daniel W. Bougie

Language

en

Proquest ID

AAI9126180

File Format

application/pdf

File Size

107 pages

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