State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University , Lanzhou 730000, China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.
Org Lett. 2016 May 20;18(10):2447-50. doi: 10.1021/acs.orglett.6b00989. Epub 2016 May 10.
We present the application of a bioinspired collective synthesis strategy in the total syntheses of seven iboga-type indole alkaloids: (±)-tabertinggine, (±)-ibogamine, (±)-ibogaine, (±)-ibogaine hydroxyindolenine, (±)-3-oxoibogaine hydroxyindolenine, (±)-iboluteine, and (±)-ervaoffines D. In particular, tabertinggine and its congeners serve as iboga precursors for the subsequent biomimetic transformations into other iboga-type alkaloids.
(±)-塔别廷碱、(±)-伊博加明、(±)-伊博苷、(±)-伊博苷羟基吲哚啉、(±)-3-氧代伊博苷羟基吲哚啉、(±)-伊波罗汀和(±)-埃罗瓦芬 D。特别是,塔别廷碱及其同系物作为伊博加的前体,用于后续的仿生转化为其他伊博加类型生物碱。