Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

William J. Kerr, Angus J. Morrison, Laura C. Paterson

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Biologically active α-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson–Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target. Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton.
Original languageEnglish
Pages (from-to)5356–5361
Number of pages6
Issue number33
Early online date6 Jun 2015
Publication statusPublished - 19 Aug 2015


  • cobalt
  • cyclisation
  • α-methylene cyclopentanone
  • Pauson-Khand
  • samarium

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