Catalytic enantioselective alkylative dearomatization-annulation: total synthesis and absolute configuration assignment of hyperibone K

J Am Chem Soc. 2010 Oct 6;132(39):13642-4. doi: 10.1021/ja1057828.

Abstract

The asymmetric total synthesis of the polyprenylated acylphloroglucinol hyperibone K has been achieved using an enantioselective alkylative dearomatization-annulation process. NMR and computational studies were employed to probe the mode of action of a chiral phase-transfer (ion pair) catalyst.

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

  • Adamantane / analogs & derivatives*
  • Adamantane / chemical synthesis
  • Adamantane / chemistry
  • Alkylation
  • Catalysis
  • Crystallography, X-Ray
  • Hemiterpenes / chemical synthesis*
  • Hemiterpenes / chemistry
  • Models, Molecular
  • Molecular Structure
  • Phloroglucinol / analogs & derivatives*
  • Phloroglucinol / chemical synthesis*
  • Phloroglucinol / chemistry
  • Stereoisomerism

Substances

  • Hemiterpenes
  • hyperibone K
  • Phloroglucinol
  • Adamantane