Total Synthesis and Structural Revision of Antibiotic CJ-16,264

Angew Chem Int Ed Engl. 2015 Aug 3;54(32):9203-8. doi: 10.1002/anie.201504337. Epub 2015 Jun 19.

Abstract

The total synthesis and structural revision of antibiotic CJ-16,264 is described. Starting with citronellal, the quest for the target molecule featured a novel bis-transannular Diels-Alder reaction that casted stereoselectively the decalin system and included the synthesis of six isomers before demystification of its true structure.

Keywords: antibiotic; natural products; structural revision; total synthesis; transannular Diels-Alder reaction.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Crystallography, X-Ray
  • Cycloaddition Reaction
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Conformation
  • Naphthalenes / chemistry
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Stereoisomerism

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • CJ-16,264
  • Lactones
  • Naphthalenes
  • Pyrazoles
  • decalin