Synthesis of bridged oxafenestranes from pleuromutilin

Robert W. Hicklin, Tania L. Lõpez Silva, Paul J. Hergenrother

Research output: Contribution to journalArticlepeer-review


Fenestranes are an intriguing class of highly strained molecules possessing a quaternary carbon with bonds that deviate from the canonical tetrahedral geometry. Herein we report the discovery that the natural product pleuromutilin can be used as a structurally complex starting material for the synthesis of a series of bridged cis,cis,cis,cis-[]- and cis,cis,cis,cis-[] oxafenestranes through a carbocation rearrangement cascade. X-ray crystallographic analysis of several cis,cis,cis,cis-[]oxafenestranes shows a significant planarization of the central tetracoordinate carbon atom and demonstrates the influence of bridgehead substituents and bridging rings on planarity.

Original languageEnglish (US)
Pages (from-to)9880-9883
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number37
StatePublished - Sep 8 2014


  • fenestranes
  • natural products
  • planar tetracoordinate carbon atom
  • strained molecules

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)


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