Department of Medicinal Chemistry, School of Pharmacy, Hebei Medical University, 361 East Zhongshan Road, Shijiazhuang 050017, P. R. China.
School of Basic Medical Sciences, Peking University, 38 Xueyuan Road, Beijing 100191, P. R. China.
Org Lett. 2022 Jul 29;24(29):5381-5385. doi: 10.1021/acs.orglett.2c02060. Epub 2022 Jul 17.
Herein, we report an unprecedented intramolecular cross-nucleophile coupling strategy of indole tethered β-amino acrylates using a catalyst system combining λ-iodanes and Lewis acids to achieve the chemodivergent synthesis of three unique alkaloid skeletons. It was worth noting that the acquisition of spiroindolenines and azepino[4,5-]indoles derivatives was switchable with choice of the Lewis acids. Moreover, the polycyclic spiroindolines containing a lactone fragment could also be accessed for the first time via cross-nucleophile coupling cascade intramolecular condensation sequence.
在此,我们报告了一种前所未有的吲哚连接的β-氨基丙烯酸酯的分子内交叉亲核耦合策略,使用包含 λ-碘烷和路易斯酸的催化剂体系来实现三种独特生物碱骨架的化学发散合成。值得注意的是,路易斯酸的选择可以实现螺吲哚啉和氮杂[4,5-]吲哚衍生物的可切换获得。此外,通过交叉亲核耦合级联分子内缩合序列,还可以首次获得含有内酯片段的多环螺吲哚啉。