Amino acid-derived natural products are ubiquitous in nature and commonly possess antibiotics or anticancer properties. In this presentation, several chemical and biocatalytic syntheses of amino acid-derived natural products will be discussed.  First, a chemoenzymatic synthesis of 13-oxoverruculogen, an anticancer endoperoxide, is achieved using enzymatic C-H peroxidation and transition metal catalyzed C-C bond activation reactions. Central to the synthesis involves the use of a substrate analog for enzymatic endoperoxidation to accomplish the synthesis of 13-oxoverruculogen in ten steps.

The second part of this presentation describes the chemical synthesis of amino acid-derived natural products containing thioaminoketals. Enteropeptin A is an antimicrobial peptide natural product with undefined stereochemical configuration at its thioaminoketal stereocenter. The total synthesis of this compound results in its structural elucidation and the determination of the stereochemical configuration of enteropeptin A.