Unified Synthesis of 10-Oxygenated <i>Lycopodium</i> Alkaloids: Impact of C<sub>10</sub>-Stereochemistry on Reactivity


The pronounced impact of the C<sub>10</sub> stereochemistry on the successful construction of a polycyclic <i>Lycopodium</i> alkaloid scaffold has been explored. A wide range of reaction conditions and functionality were investigated to control a keto sulfone Michael addition to construct the C<sub>7</sub>–C<sub>12</sub> linkage. An unexpected, overriding impact of the C<sub>10</sub> stereochemistry in stereoselectivity and reaction rate in the Michael addition was observed. Furthermore, divergent reactivity of a conformationally accelerated, intramolecular Mannich cyclization based on the C<sub>10</sub> stereochemistry was discovered. The successful execution of this synthetic route resulted in the total synthesis of all three known 10-oxygenated <i>Lycopodium</i> alkaloids: 10-hydroxylycopodine, paniculine, and deacetylpaniculine

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oaioai:figshare.com:artic...Last time updated on 2/12/2018

This paper was published in FigShare.

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