A synthesis of the octalin core of integramycin, isolation of alkaloids from Amazonian plants, and polyols from renewable resources

Abstract

This document is a presentation and discussion on three projects in three parts. Part One is a detailed summary of organic chemistry efforts in the synthesis of a model of the natural product integramycin. This concludes six years of work on various synthetic routes and analysis of spontaneous Diels-Alder chemistry. The goal was to probe part of our group's larger biosynthetic hypothesis concerning spontaneity in the biosynthesis of polyketides. Part Two summarizes the natural products chemistry that I performed while being supported by a UMN Graduate School Interdisciplinary Doctoral Fellowship. This was a year-long effort (academic year 2010-2011) in identifying the main chemical components of various plant samples from the Amazon. The goal was to isolate new natural products, elucidate their novel structures, and study the biological activity of these constituents. Part Three is a summary of the advances I made as a polymer chemist through the support of the UMN Center for Sustainable Polymers. This work began in the summer of 2010 and includes the investigation of both soybean oil and natural terpenoids as precursors to polyols for use in polyurethanes. The goal was to prepare sustainable polyurethanes for flexible foam applications.