Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization

被引：38
|
作者：
Zhang, Zhiguo [1 ]
Song, Xiaoqing [1 ]
Li, Guofeng [1 ]
Li, Xiang [1 ]
Zheng, Dan [2 ]
Zhao, Xuna [1 ]
Miao, Huanran [1 ]
Zhang, Guisheng [1 ]
Liu, Lantao [3 ]
机构：
[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Sch Chem & Chem Engn,Minist Educ, Henan Key Lab Organ Funct Mol & Drug Innovat,Key, Xinxiang 453007, Henan, Peoples R China
[2] Qual & Tech Supervis Inspect & Testing Ctr Xuchan, Xuchang 461000, Peoples R China
[3] Shangqiu Normal Univ, Coll Chem & Chem Engn, Shangqiu 476000, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Spiro-indolines; Fused indolines; 2-Iodoxybenzoic acid; Hypervalent iodine reagents; ASYMMETRIC TOTAL-SYNTHESIS; UNACTIVATED ALKENES; EFFICIENT SYNTHESIS; IODINE(V) REAGENTS; ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; CONSTRUCTION; ALKALOIDS; HYDROCARBOFUNCTIONALIZATION; HYDROCARBAZOLE;
D O I：
10.1016/j.cclet.2020.11.001
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report a 2-iodoxybenzoic acid (IBX)-mediated intarmolecular oxidative spiro-fused tandem cyclization reaction of tryptophan analogs bearing an N-arylamides side-chain to rapidly afford polycyclic spiroindolines featuring multiple stereocenters including a quaternary stereocenters under mild reaction conditions. Among them, a novelty azaphosphol idine-containing spiroindoline compound is synthesized for the first time. It may open the door to azaphos pholidine-containing spiroindoline compound of potential interest in synthetic and medicinal chemistry. A plausible mechanism is proposed. (c)& nbsp;2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：1423 / 1426
页数：4
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