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Synthetic Study of Dragmacidin E: Construction of the Core Structure Using Pd-Catalyzed Cascade Cyclization and Rh-Catalyzed Aminoacetoxylation

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posted on 2017-02-20, 00:00 authored by Naoya Inoue, Shun-ichi Nakano, Shingo Harada, Yasumasa Hamada, Tetsuhiro Nemoto
We developed a novel synthetic method of the core structure of dragmacidin E bearing a 7-membered ring-fused bis­(indolyl)­pyrazinone skeleton. Formation of the 7-membered ring-fused tricyclic indole skeleton was accomplished using a palladium-catalyzed Heck insertion–allylic amination cascade. Vicinal difunctionalization of the 7-membered ring was realized via a rhodium-catalyzed aminoacetoxylation.

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