Synthesis of Tricyclo[4,3,1,01,5]decane Core of Plumisclerin A Using Pauson-Khand Annulation and SmI2-Mediated Radical Cyclization

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Abstract

An efficient synthesis of the tricyclo[4,3,1,01, 5]decane core (B/C/D rings) of plumisclerin A, a unique cytotoxic marine diterpenoid, is described. A Pauson-Khand reaction and a SmI2-mediated radical 1,4-conjugate addition successfully served as key reactions for construction of the fully functionalized 5,6-fused rings and the highly strained cyclobutanol moiety with correct relative stereochemistries, respectively.

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Chen, J. P., He, W., Yang, Z. Y., & Yao, Z. J. (2015). Synthesis of Tricyclo[4,3,1,01,5]decane Core of Plumisclerin A Using Pauson-Khand Annulation and SmI2-Mediated Radical Cyclization. Organic Letters, 17(14), 3379–3381. https://doi.org/10.1021/acs.orglett.5b01563

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