New Strategies for the Synthesis of Unusual Peptides and Alkaloids

The complex structures of peptide and alkaloid natural products provide inspiration for the development of new methods in synthetic organic chemistry. Additionally, the potent and selective bioactivity of many of these compounds provides opportunities to use organic synthesis to answer important questions in chemical biology. Results from our synthetic efforts targeting the peptide yaku’amide A and related analogs will be presented, and the anticancer activity of these compounds will be discussed. In addition, our efforts to use the methodology developed in this endeavor to evaluate the ability of dehydroamino acids to increase the proteolytic stability of peptides will be described.

Microwave-promoted reactions of iminyl radicals provide straightforward and efficient means of constructing nitrogen-containing compounds. Our results in this area will be presented, including iminyl radical fragmentations and cyclizations. Application of a novel iminyl radical cascade reaction to the synthesis of the alkaloid virosinine A will be described.