Thesis advisor: James P. Morken / This dissertation describes the development of a method for the stereoselective synthesis of organoboronates and the applications of these products to target-oriented synthesis. The first chapter discusses an investigation of the palladium-catalyzed conjunctive cross-coupling reaction by kinetic analysis. This reaction enables the asymmetric synthesis of organoboronates by utilizing the 1,2-metallate rearrangement of borates as a mechanistic step in a cross-coupling reaction. The second chapter describes the application of the conjunctive cross-coupling reaction to the asymmetric synthesis of tertiary boronic esters. In chapter three, the conjunctive cross-coupling reaction of 1,2-disubstituted alkenyl boronates is presented. Such a substrate class is susceptible to the undesired Suzuki-Miyaura cross-coupling reaction, and this challenge led to the development of a novel diol ligand for boron as an effective solution. The final chapter details the progress toward the total synthesis of the sarcodictyin natural products, which display promising anti-cancer activity. The synthetic route utilizes reactions of organoboronates for powerful C–C bond formations; the construction of a fully-cyclyzed advanced intermediate is achieved in eight steps. / Thesis (PhD) — Boston College, 2020. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_108724 |
| Date | January 2020 |
| Creators | Myhill, Jesse Alexander |
| Publisher | Boston College |
| Source Sets | Boston College |
| Language | English |
| Detected Language | English |
| Type | Text, thesis |
| Format | electronic, application/pdf |
| Rights | Copyright is held by the author. This work is licensed under a Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0). |
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