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

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

Research output: Contribution to journalArticle

3 Citations (Scopus)
67 Downloads (Pure)

Abstract

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
JournalTetrahedron
Volume71
Issue number33
Early online date6 Jun 2015
DOIs
Publication statusPublished - 19 Aug 2015

Keywords

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

Fingerprint Dive into the research topics of 'Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry'. Together they form a unique fingerprint.

  • Projects

    Cite this