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Bioinspired Electrochemical Cyclization toward the Divergent Synthesis of Mavacurane- and Akuammiline-Type Alkaloids
Eisuke Sato1, Tomohiro Nakahama1, Yuika Nomura1
1Department of Applied Chemistry, Graduate School of Environmental, Life, Natural Science and Technology, Okayama University, 3-1-1, Tsushima-naka, Kita-ku, Okayama, 700-8530, Japan.
Abstract:
We report a divergent electrochemical strategy for the bioinspired synthesis of mavacurane- and akuammiline-type alkaloid frameworks from a common indole-malonate precursor. By tuning the redox mediator, selective N-C or C-C bond formation was achieved. Iodide-mediated electrolysis promoted iodination of the malonate carbanion, followed by intramolecular nucleophilic cyclization to furnish the mavacurane core. In contrast, ferrocene-mediated oxidation generated a malonate-centered radical that afforded the akuammiline skeleton.
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