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Date of Award

Spring 2009

Document Type

Restricted Thesis: Campus only access

Degree Name

Bachelor of Science


Biochemistry & Molecular Biol.

First Advisor

Dr. John Gupton


Interest about the marine alkaloids, such as the Ningalins and the Rigidins, has developed due to their interesting biological activity. The Gupton group has previously reported the syntheses of Ningalin B, Rigidin and Rigidin E, as well as a number of related pyrrole containing natural products. The novel synthetic route to Ningalin B relies on the formation of a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt derivative. Our previous strategy for the successful synthesis of Rigidin also involved vinylogous iminium salt precursors. Each pyrrole substituent is introduced independently and can easily be varied to accommodate studies for Rigidin analogs. We anticipate that this same strategy can be utilized for the synthesis of the remaining members of this family of alkaloids, Rigidin B, C, and D. The synthesis of these marine alkaloids has unveiled related pyrrole compounds possessing interesting biological properties. JG-03.14 and its analogs are of prime interest to our research group for its tubulin inhibiting properties and cytotoxic activity against certain cancer strains.