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

页码：1423 / 1426

页数：4

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