Total synthesis of cristatic acid

Org Lett. 2000 Aug 10;2(16):2467-70. doi: 10.1021/ol0061236.

Abstract

The first total synthesis of cristatic acid 1, an antibiotic endowed with considerable activity against Gram-positive bacteria, hemolytic properties, and significant cytotoxicity, is described. Key to success are the formation of its 2,4-disubstituted furan moiety via a palladium-catalyzed alkylation of vinylepoxide 10 derived from sulfonium salt 8 and the use of SEM ethers as the protecting groups for the phenolic OH functions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / pharmacology
  • Gram-Positive Bacteria / drug effects
  • Indicators and Reagents
  • Models, Molecular
  • Molecular Conformation
  • Salicylates / chemical synthesis
  • Salicylates / chemistry
  • Salicylates / pharmacology

Substances

  • Anti-Bacterial Agents
  • Furans
  • Indicators and Reagents
  • Salicylates
  • cristatic acid