Stereochemistry of gamma-amino-beta-hydroxy acids of natural and synthetic origin

Abstract

The following dissertation will discuss my contribution to research in the area of structure elucidation, specifically dealing with the configurational assignment of γ-amino-β-hydroxy acid derivatives. Our investigations have unveiled a simple 1H NMR methodology useful for assigning the relative configuration of the intact moiety. In an effort to validate a general method for the complete configurational assignment of statine derivatives, we have performed an extensive time course study on the hydrolysis rates of the statine derivatives. These investigations have led us to propose a reliable, general and optimal approach for complete configurational assignment of the most common naturally occurring statine derivatives. Finally, a total synthesis of the stictamide A and B and evaluation of biological activities are presented. The synthesis of these natural products provides evidence to support of the originally proposed structures and expands the scope of the 1H NMR methodology useful for assigning the configuration of statine derivatives.