Synthesis of bridged oxafenestranes from pleuromutilin

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

Research output: Contribution to journalArticle

Abstract

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-[4.5.5.5]- and cis,cis,cis,cis-[4.5.7.5] oxafenestranes through a carbocation rearrangement cascade. X-ray crystallographic analysis of several cis,cis,cis,cis-[4.5.5.5]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
Volume53
Issue number37
DOIs
StatePublished - Sep 8 2014

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Synthesis of bridged oxafenestranes from pleuromutilin'. Together they form a unique fingerprint.

  • Cite this