Total Synthesis of (±)-Trigonoliimine C via Oxidative Rearrangement of an Unsymmetrical Bis-Tryptamine

We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis-tryptamine.

本研究首次报道了(±)-三角叶吲哚碱C（(±)-trigonoliimine C）的全合成。该化合物隶属于一类结构复杂的生物碱家族，本合成以色胺（tryptamine）与6-甲氧基色胺（6-methoxytryptamine）为起始原料，仅需10步反应即可完成。本次研究所采用的汇聚式合成策略，核心依托于非对称2,2'-双色胺（2,2′-bis-tryptamine）的选择性氧化重排反应。