Enantioselective Total Synthesis of Hyperforin

J Am Chem Soc. 2013 Jan 16;135(2):644-7. doi: 10.1021/ja312150d. Epub 2012 Dec 31.

Abstract

A modular, 18-step total synthesis of hyperforin is described. The natural product was quickly accessed using latent symmetry elements, whereby a group-selective, Lewis acid-catalyzed epoxide-opening cascade cyclization was used to furnish the bicyclo[3.3.1]nonane core and set two key quaternary stereocenters.

Publication types

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

MeSH terms

  • Bridged Bicyclo Compounds / chemistry
  • Cyclization
  • Lewis Acids / chemistry
  • Molecular Structure
  • Phloroglucinol / analogs & derivatives*
  • Phloroglucinol / chemical synthesis
  • Phloroglucinol / chemistry
  • Stereoisomerism
  • Terpenes / chemical synthesis*
  • Terpenes / chemistry

Substances

  • Bridged Bicyclo Compounds
  • Lewis Acids
  • Terpenes
  • Phloroglucinol
  • hyperforin