The malagasy alkaloids are a family of strychnos alkaloids whose members have been shown to potentiate chloroquine (CQ) activity against previously resistant strains of Plasmodium falciparum malaria. 11-Demethoxymyrtoidine (1), myrtoidine (2), and malagashanine (3) were isolated during a study to identify the major bioactive components of Madagascan shrub strychnos myrtoides, whose bark is used by local populations to treat CQ resistant malaria. Herein we report significant progress toward the first total syntheses of 1 and 2. Our convergent strategy involves an iminium ion cascade annulation reaction to diastereoselectively assemble the tetracyclic core of these alkaloids, including the synthetically challenging trans fusion between the C and D rings.

Progress toward the total synthesis of 11-demethoxymyrtoidine and myrtoidine

255th National Meeting (2018)

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