Date of Award
Doctor of Philosophy
George A. Kraus
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.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Daniel W. Bougie
Bougie, Daniel W., "Approaches to indole alkaloids " (1991). Retrospective Theses and Dissertations. 9923.