Total synthesis of virgatolide B via exploitation of intramolecular hydrogen bonding

J Org Chem. 2014 Jun 6;79(11):5269-81. doi: 10.1021/jo5008527. Epub 2014 May 23.


A full account of the enantioselective total synthesis of virgatolide B is reported. Key features of the synthesis include an sp(3)-sp(2) Suzuki-Miyaura cross-coupling of a β-trifluoroboratoamide with an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction. Intramolecular hydrogen bonding governed the regioselectivity of the key spiroketalization step, affording the natural product as a single regioisomer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Hydrogen Bonding
  • Molecular Structure
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry*
  • Stereoisomerism


  • Furans
  • Spiro Compounds
  • virgatolide B