Asymmetric Synthesis and Novel Transformations of 2-Oxetanones

Texas A&M Research Foundation, College Station TX

Investigators

Abstract

Professor Daniel Romo in the Department of Chemistry at Texas A&M University is supported by the Organic and Macromolecular Chemistry Program for his development of concise and practical enantioselective syntheses of beta-lactones via nucleophile catalyzed aldol-lactonizations (NCALs) of ketenes and aldehydes. Novel transformations of these beta-lactones to form various heterocyclic structures will be explored. The utility of the intramolecular NCAL reaction will be illustrated by the total synthesis of a lactacystin analog and an enantioselective synthesis of the natural product, brefeldin A. Mechanistic studies on the NCAL reaction will be carried out using REACT IR and 1H NMR. With the support of the Organic and Macromolecular Program, Professor Romo is developing novel methods by which certain highly strained organic compounds can be prepared with precise control of their three-dimensional structure. These compounds serve as intermediates which can be further converted to more complex products, many of which are share similar structural features with pharmacologically active compounds.