Total synthesis of (18S)- and (18R)-homolargazole by rhodium-catalyzed hydrocarboxylation

Chemistry. 2014 Feb 17;20(8):2164-8. doi: 10.1002/chem.201303300. Epub 2014 Jan 29.

Abstract

Homolargazole derivatives, in which the macrocycle of natural largazole is extended by one methylene group, were prepared by the recently developed rhodium-catalyzed hydrocarboxylation reaction onto allenes. This strategy gives access to both the (18S)- and (18R)-stereoisomers in high stereoselectivity under ligand control.

Keywords: macrocyclic compounds; medicinal chemistry; rhodium; stereoselective catalysis; synthetic drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkadienes / chemistry*
  • Catalysis
  • Depsipeptides / chemical synthesis*
  • Depsipeptides / chemistry
  • Ligands
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Alkadienes
  • Depsipeptides
  • Ligands
  • Thiazoles
  • largazole
  • propadiene
  • Rhodium