title: An Indoxyl-Based Strategy for the Synthesis of Indolines and Indolenines.
abstract: An indoxyl-based strategy for the synthesis of indolines and indolenines via unprecedented aza-pinacol and aza-semipinacol rearrangements was developed. This method provides direct access to the core structures of several classes of indole alkaloids. The synthetic utility was demonstrated by the divergent synthesis of an array of functionalized polycyclic structures from a common intermediate and the formal total synthesis of the indoline natural product minfiensine. The reversed reactivity of indoxyl as a building block compared to that of indole offers a conceptually distinct disconnection strategy for indoline- and indolenine-containing heterocycles and natural products.
authors: Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China).
authors: Yuanyuan
authors: Y
authors: Yu
authors: Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China).
authors: Guang
authors: G
authors: Li
authors: Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China).
authors: Long
authors: L
authors: Jiang
authors: Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China). zuliansuo@biomed.tsinghua.edu.cn.|Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu (China). zuliansuo@biomed.tsinghua.edu.cn.
authors: Liansuo
authors: L
authors: Zu
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001372:Aza Compounds; D001688:Biological Products; D002227:Carbazoles; D053138:Cyclohexenes; D026121:Indole Alkaloids; D007211:Indoles; D009842:Oligopeptides; C414027:aza-pinacol; C504098:minfiensine; C519041:semipinacol; C034082:indoxyl; C057812:indoline
keywords: aza-pinacol rearrangement; indolenines; indolines; indoxyl; synthetic methods