Total Synthesis of Carolacton and Demethylcarolactons with Potent Antiviral Activity

Org Lett. 2024 Jan 12;26(1):370-375. doi: 10.1021/acs.orglett.3c04038. Epub 2024 Jan 3.

Abstract

Carolacton, a naturally occurring MTHFD1 inhibitor, exhibits potent inhibitory activity against various RNA viruses including SARS-CoV-2. Herein, we present a concise total synthesis of carolacton, featuring the Krische allylation, Marshall coupling, NHK coupling, and RCM reaction as key elements. Additionally, we have synthesized three simplified carolacton analogues, one of which, namely, 14-demethyl-carolacton, exhibited notable antiviral activity. The present work paves the way for further exploration of the therapeutic potential of carolacton and its analogues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents* / pharmacology
  • Macrolides* / pharmacology

Substances

  • carolacton
  • Macrolides
  • Antiviral Agents