Total Synthesis and Structure Revision of Boholamide A

Org Lett. 2021 Jul 2;23(13):4976-4980. doi: 10.1021/acs.orglett.1c01382. Epub 2021 Jun 10.

Abstract

The 15-membered cyclic depsipeptide boholamide A and an epimer were prepared by total synthesis for the first time, thus leading to a revision of C6 stereochemistry in the originally proposed structure of natural boholamide A. This convergent route features achievement of a macro-lactamization step in a gram scale. The revised boholamide A was sythesized with 16 linear steps in 5.46% overall yield. This work facilitates the investigations of boholamide A as a potential hypoxia-selective anticancer agent.

Publication types

  • Research Support, Non-U.S. Gov't