Development of New Anionic Cascades and Analysis of US FDA Drug Architectures

Abstract

This dissertation is divided into five chapters, encompassing innovative synthetic contributions in the area of Darzens annulations, anionic-amino-Cope cascades, structural analysis of FDA-approved pharmaceuticals as well as book chapter contributions in highlighting synthetic contributions in oxirane and aziridine chemistry. Chapter 1 presents two-book chapter contributions made which highlight synthetic contributions made with oxiranes and aziridines. Part 1: focuses on synthetic contributions made with oxiranes (epoxides) from 2008-2018. Part II focuses on homologation approaches to access oxiranes and aziridines from carbonyl and imines. Chapter II presents two-published perspectives, published in the Journal of Medical Chemistry. Part I analyzes oxygen-heterocycles seen in FDA-approved pharmaceuticals. Part II analyzes the structural diversity in FDA-approved combination drugs. Chapter III: presents novel contributions made in the arena of anionic-amino-Cope rearrangements (Part I) and applications (Part II). Chapter IV presents novel contributions made with vinylogous (Aza)-Darzens annulations. Part I discusses an asymmetric-vinylogous Aza-Darzens protocol with a bromo-butenolide nucleophile. Part II describes phenyl sulfone-containing vinylogous (Aza)-Darzens routes. Chapter V describe mild protocols to obtain trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes.