New tricks in amino acid synthesis: Applications to complex natural products

ORGN 270

Robert M Williams, rmw@lamar.colostate.edu, Chemistry, Colorado State University, Fort Collins, CO 80523
Our laboratory has developed a range of synthetic methodologies and strategies for utilization in tackling the total synthesis of several naturally occurring nitrogenous substances of both biomedical significance and biological intrigue. Optically active glycine templates based on diphenyloxazinones, have been extensively developed in our laboratory for various manifolds of chemical reactivity for the asymmetric synthesis of α-amino acids, peptide isosteres and numerous complex amino acid-containing natural products. To date, our laboratory has developed and exploited the reactivities of the glycine templates as: (1) glycine electrophiles, (2) glycine enolates, (3) glycine radicals, (4) azomethie ylids, (5) glycine phosphonates, (6) α,β-dehydroamino acid templates, and (7) oxocarbenium ion templates for the asymmetric synthesis of peptide isosteres. The total synthesis of several select natural products and current approaches to the total synthesis quinine, palau'amine, nakadomarin A, tuberostemoninol and others will be described.