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

2 Citations (Scopus)

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.
LanguageEnglish
Pages5356–5361
Number of pages6
JournalTetrahedron
Volume71
Issue number33
Early online date6 Jun 2015
DOIs
Publication statusPublished - 19 Aug 2015

Fingerprint

Cyclization
Sulfides
Skeleton
Metals
samarium diiodide
cyclopentenone

Keywords

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

Cite this

Kerr, William J. ; Morrison, Angus J. ; Paterson, Laura C. / Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry. In: Tetrahedron. 2015 ; Vol. 71, No. 33. pp. 5356–5361.
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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.",
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Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry. / Kerr, William J.; Morrison, Angus J.; Paterson, Laura C.

In: Tetrahedron, Vol. 71, No. 33, 19.08.2015, p. 5356–5361.

Research output: Contribution to journalArticle

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AU - Morrison, Angus J.

AU - Paterson, Laura C.

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KW - cobalt

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KW - Pauson-Khand

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