Document Type
Thesis
Date of Degree Completion
Spring 2017
Degree Name
Master of Science (MS)
Department
Chemistry
Committee Chair
Timothy K. Beng
Second Committee Member
Levente Fabry-Asztalos
Third Committee Member
Gil Belofsky
Abstract
The synthesis and evaluation of structure-activity relationships of saturated nitrogen heterocycles is the focal point of various pharmaceutical companies thanks to the high biological activity of previously isolated azacycles. Here, we describe an operationally simple and highly efficient approach to macrocyclic lactams bearing vicinal stereocenters and a challenging cycloalkyne motif. The outcomes are achieved through a novel [4 + 2] cycloaddition reaction between an N-iodoarylated-1,3-azadiene and cyclic anhydrides, followed by interception of the cycloadducts in cross-coupling manifolds (e.g., Sonogashira coupling) and concomitant lithiation-cyclization of the tethered alkyne. An unprecedented example of a hydroamino alkylation that is transition metal-free and occurs at room temperature will also be discussed.
Recommended Citation
Mansker, Brandon Joseph, "Chemoselective and Stereoselective Exploration of the Chemical Reactivity Space of Castagnoli-Cushman-Derived Allylic Lactamoyl Esters: Application to the Synthesis of Aza-Polycyclic Architectures" (2017). All Master's Theses. 704.
https://digitalcommons.cwu.edu/etd/704
Language
English
Included in
Chemical Actions and Uses Commons, Heterocyclic Compounds Commons, Medicinal and Pharmaceutical Chemistry Commons, Organic Chemicals Commons, Polycyclic Compounds Commons