Discovery and Bioinspired Synthesis of Salpratone A

J Org Chem. 2024 Feb 2;89(3):1858-1863. doi: 10.1021/acs.joc.3c02584. Epub 2024 Jan 12.

Abstract

Salpratone A (1), a novel abietane diterpenoid containing a unique cis-fused A/B ring, was isolated from Salvia prattii. Bioactivity studies showed that 1 has potent activity in inhibiting platelet aggregation induced by multiple agonists as well as antithrombotic efficacy in the FeCl3-induced rat in vivo thrombosis model. Furthermore, a bioinspired synthesis of 1 from the abundant natural product ferruginol was achieved in 6 steps with a 22% overall yield. The key steps include a stereoselective allyl oxidation and a subsequent regioselective Meinwald rearrangement.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abietanes* / chemical synthesis
  • Animals
  • Rats
  • Salvia* / chemistry

Substances

  • Abietanes