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

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Kerr, William J. and Morrison, Angus J. and Paterson, Laura C. (2015) Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry. Tetrahedron, 71 (33). 5356–5361. ISSN 0040-4020 (https://doi.org/10.1016/j.tet.2015.06.003)

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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.

ORCID iDs

Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Morrison, Angus J. and Paterson, Laura C.;
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