Total Synthesis of Kehokorins A-E, Cytotoxic p-Terphenyls

J Org Chem. 2017 Mar 17;82(6):3159-3166. doi: 10.1021/acs.joc.7b00147. Epub 2017 Mar 7.

Abstract

This paper describes a general method for the synthesis of kehokorins A-E, novel cytotoxic p-terphenyls. 2,4,6-Trihydroxybenzaldehyde served as a common building block for preparation of the central aromatic ring. Construction of their p-terphenyl skeletons was achieved by a stepwise Suzuki-Miyaura coupling, whereas the phenyldibenzofuran moiety was built up by an intramolecular Ullmann reaction. Introduction of an l-rhamnose residue into partly protected kehokorin B was performed by the trichloroacetimidate method.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Terphenyl Compounds / chemical synthesis*
  • Terphenyl Compounds / chemistry
  • Terphenyl Compounds / pharmacology

Substances

  • Terphenyl Compounds