Transition metal-mediated carbon-carbon bond forming reactions are among the most synthetically useful chemical transformations in modern organic synthesis. The most expedient routes toward many natural products and compounds of pharmacological interest involve such reactions. Our research focuses on the development of a novel synthetic route towards the total synthesis of the novel antibacterial natural product trocheliophorolide A using such transition metal-mediated reactions. Specifically, trocheliophorolide A was envisioned to be synthesized via a Stille coupling between a butenolide and an unsaturated sidechain. The butenolide synthesis was optimized and several routes to synthesize the sidechain were investigated. This thesis will detail the ongoing synthesis of trocheliophorolide A using a Wittig reaction rather than the previously envisioned Corey-Fuchs reaction, as well as suggestions towards the completion of the total synthesis.
Library of Congress Subject Headings
Lactones--Synthesis; Ketones--Synthesis; Organic compounds--Synthesis; Antibacterial agents
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Dorn, Stephanie, "Studies toward the total synthesis of Trocheliophorolide A" (2011). Thesis. Rochester Institute of Technology. Accessed from
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