Thesis advisor: Amir H. Hoveyda / The possibility of accessing altered frameworks wherein the spatial relationship between several organic fragments can be controlled can notably impact drug discovery and development. In this context, we introduce a strategy that can be used for programmable and divergent synthesis of a diverse and otherwise difficult-to-prepare set of cyclic amines and bridged bicyclic enamines wherein up to four exit vectors can be altered accordingly. Central to the approach is a catalytic multicomponent reaction that merges a nitrile, a trisubstituted allenylboronate and a silyl hydride, delivering multifunctional 1,4-aminoboronates that contain a versatile and stereochemically defined trisubstituted alkenyl boronate. We show that the products can be modified to afford an assortment of complex, drug-like, polycyclic amines. What is more, a new cyclization strategy, involving the triflic anhydride-mediated reaction of a trisubstituted alkene and a nearby amide, was developed for synthesis of the corresponding bridged bicyclic scaffolds. These resulting bridged enamines and various derivatives are evocative of the 1-azabicyclo[3.2.1]octane core, found in a variety of bioactive alkaloids. / Thesis (PhD) — Boston College, 2023. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.
| Identifer | oai:union.ndltd.org:BOSTON/oai:dlib.bc.edu:bc-ir_109781 |
| Date | January 2023 |
| Creators | Ponzi, Ryan P. |
| 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, with all rights reserved, unless otherwise noted. |
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