Asymmetric total synthesis of trilobacin via organoselenium-mediated oxonium ion formation/SiO2-promoted fragmentation

J Am Chem Soc. 2010 Sep 8;132(35):12226-7. doi: 10.1021/ja106116v.

Abstract

An asymmetric total synthesis of trilobacin (1), an annonaceous acetogenin with potent anticancer activities, was accomplished wherein the construction of its erythro-bis(2,2')-tetrahydrofuran core 2 featured a novel organoselenium-mediated oxonium ion formation/SiO(2)-promoted fragmentation of alpha,alpha'-cis-oxocene 3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Ions / chemistry
  • Molecular Conformation
  • Organoselenium Compounds / chemistry*
  • Oxocins / chemistry*
  • Silicon Dioxide / chemistry*
  • Stereoisomerism

Substances

  • Furans
  • Ions
  • Organoselenium Compounds
  • Oxocins
  • trilobacin
  • Silicon Dioxide