Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin

Org Lett. 2020 Jul 17;22(14):5550-5554. doi: 10.1021/acs.orglett.0c01913. Epub 2020 Jun 29.


The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels-Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork-Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access to (-)-anthracimycin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry*
  • Chemistry Techniques, Synthetic
  • Esterification
  • Polyketides / chemical synthesis*
  • Polyketides / chemistry*
  • Stereoisomerism


  • Anti-Bacterial Agents
  • Biological Products
  • Polyketides
  • anthracimycin