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Total Synthesis, Relay Synthesis, and Structural Confirmation of the C18-Norditerpenoid Alkaloid Neofinaconitine

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    Total Synthesis, Relay Synthesis, and Structural Confirmation of the C18-Norditerpenoid Alkaloid Neofinaconitine
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    † ‡ †Tri-Institutional PhD Program in Chemical Biology, ‡Molecular Pharmacology & Chemistry Program, and Tri-Institutional Research Program, Memorial Sloan−Kettering Cancer Center, 1275 York Avenue, Box 422, New York, New York 10065, United States
    [email protected]; [email protected]
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    Cite this: J. Am. Chem. Soc. 2013, 135, 38, 14313–14320
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    https://doi.org/10.1021/ja4064958
    Published September 16, 2013
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    Abstract

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    The first total synthesis of the C18-norditerpenoid aconitine alkaloid neofinaconitine and relay syntheses of neofinaconitine and 9-deoxylappaconitine from condelphine are reported. A modular, convergent synthetic approach involves initial Diels–Alder cycloaddition between two unstable components, cyclopropene 10 and cyclopentadiene 11. A second Diels–Alder reaction features the first use of an azepinone dienophile (8), with high diastereofacial selectivity achieved via rational design of siloxydiene component 36 with a sterically demanding bromine substituent. Subsequent Mannich-type N-acyliminium and radical cyclizations provide complete hexacyclic skeleton 33 of the aconitine alkaloids. Key endgame transformations include the installation of the C8-hydroxyl group via conjugate addition of water to a putative strained bridghead enone intermediate 45 and one-carbon oxidative truncation of the C4 side chain to afford racemic neofinaconitine. Complete structural confirmation was provided by a concise relay synthesis of (+)-neofinaconitine and (+)-9-deoxylappaconitine from condelphine, with X-ray crystallographic analysis of the former clarifying the NMR spectral discrepancy between neofinaconitine and delphicrispuline, which were previously assigned identical structures.

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    Cite this: J. Am. Chem. Soc. 2013, 135, 38, 14313–14320
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    https://doi.org/10.1021/ja4064958
    Published September 16, 2013
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