Synthesis of Tryptophan-Based Dimeric Diketopiperazine Alkaloids Using Bioinspired Reactions

Abstract

Tryptophan-based dimeric diketopiperazine alkaloids such as ditryptophenaline, WIN 64821, naseseazine A, and naseseazine B, exhibit a unique architecture and interesting biological activity. These alkaloids have been the subject of intense study by the synthetic organic chemistry community, and several elegant total syntheses have been discovered, especially using bioinspired strategies. Described herein is a brief overview of these alkaloid syntheses via bioinspired transformations as key steps.