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Date of Award
2014
Document Type
Restricted Thesis: Campus only access
Degree Name
Bachelor of Science
Department
Biochemistry & Molecular Biol.
First Advisor
Dr. John Gupton
Abstract
Pyrrole containing marine natural products continue to be a rich source of biologically interesting substances. The polycitones, rigidins, storniamides, ningalins and lamellarins represent pyrrole chemotypes that have been pursued from a synthetic standpoint because of their antitumor properties and their action on multi-drug resistant cancer cell lines. Here, the synthesis of a new, flexible pyrrole building block and its application to the regiospecific synthesis of tri- and tetra-substituted pyrroles is described. Optimization studies were carried out for both the synthesis of this intermediate and for determining the scope and limitations of cross- coupling aromatic residues to the pyrrole core. A preparation of regiospecific 3,4-diaryl isomers is presented as well as a formal synthesis of the natural products polycitrin A and polycitones A and B all from the same pyrrole building block.
Recommended Citation
Wormald, Michael, "Regiospecific functionalization of pyrroles using formyl-group activated suzuki coupling: application to a formal synthesis of polycitones a and b and polycitrin a" (2014). Honors Theses. 897.
https://scholarship.richmond.edu/honors-theses/897