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Convergent Total Syntheses of the Amaryllidaceae Alkaloids Lycoranine A, Lycoranine B, and 2‑Methoxypratosine

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posted on 19.02.2016, 08:42 by Hye Sun Kim, Martin G. Banwell, Anthony C. Willis
The title alkaloids, 1, 2, and 3 respectively, have been prepared in a convergent manner by two related routes. The superior one involves C–H functionalization of the relevant 5-methoxyindole at C-7 using Hartwig’s protocol and thus forming the corresponding borolated indole that could be coupled with the requisite 2-bromobenzoate to deliver the title natural products. Single crystal X-ray analyses of the synthetically derived samples of compounds 1 and 2 are reported.