Haploscleridamine is a novel tryptamine derived-alkaloid isolated from a sponge of the order haplosclerida. Haploscleridamine shows biological activity as inhibitor of cathepsin K (a novel cysteine protease that has been implicated as playing a role in osteoporosis). We report the first asymmetric total synthesis of haploscleridamine achieved in 10 steps starting from natural L-histidine. The key steps in the synthesis are; a ring closing metathesis to form the cyclohexene ring, and a Buchwald modification of the classical Fisher-indole synthesis to construct the β-carboline fragment

Asymmetric total synthesis of haploscleridamine

256th National Meeting (2018)

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