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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.
- α-methylene cyclopentanone
Kerr, W. J., Morrison, A. J., & Paterson, L. C. (2015). Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry. Tetrahedron, 71(33), 5356–5361. https://doi.org/10.1016/j.tet.2015.06.003