Biomimetic Synthesis of Myrtucommulones D-E

J Org Chem. 2025 Jun 27;90(25):8737-8744. doi: 10.1021/acs.joc.5c00859. Epub 2025 Jun 13.

Abstract

A concise and efficient biomimetic synthesis of myrtucommulones D-E has been achieved, proceeding in just 6-7 linear steps from readily available biogenetic building blocks. The key feature of the synthesis was the Zn-mediated skeletal rearrangement reaction, without the need for rare metal photocatalysts and visible light. Based on this biomimetic synthesis, four compounds demonstrated moderate to excellent cytotoxic activities against osteosarcoma cells (U2OS and 143B).

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Biomimetic Materials* / chemical synthesis
  • Biomimetic Materials* / chemistry
  • Biomimetics*
  • Catalysis
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Zinc / chemistry

Substances

  • Antineoplastic Agents
  • Zinc