Total synthesis of virgatolide B

Org Lett. 2013 Sep 6;15(17):4588-91. doi: 10.1021/ol402191t. Epub 2013 Aug 19.


The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp(3)-sp(2) Suzuki coupling of an enantiomerically enriched β-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

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


  • Furans
  • Spiro Compounds
  • spiroketal
  • virgatolide B