Four-Component Construction of Coumarin-Fused Pyrrolo[2,1-a]isoquinoline: Expedient Synthesis of Lamellarins and Their Regioselective Demethylation

被引：13

作者：

Manjappa, Kiran B. ^{[1
]}

Jhang, Jia-Wei ^{[2
]}

Lakshmi, K. C. Seetha ^{[2
]}

Yang, Ding-Yah ^{[1
,2
]}

机构：

[1] Tunghai Univ, Grad Program Biomed & Mat Sci, 1727,Sec 4,Taiwan Blvd, Taichung 407224, Taiwan

[2] Tunghai Univ, Dept Chem, 1727,Sec 4,Taiwan Blvd, Taichung, Taiwan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 01期

关键词：

1,3-Dipolar cycloaddition; Lamellarin; Multi-component reaction; Pyrrolo[2; 1-a]isoquinoline; Regioselective demethylation; ALPHA; 20-SULFATE; TOPOISOMERASE-I; DERIVATIVES; INHIBITOR; CASCADE; CYCLOADDITION; ALKALOIDS; ALKENES; CORE;

D O I：

10.1002/ajoc.202100659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Construction of the coumarin-fused pyrrolo[2,1-a]isolquinoline skeleton was realized through a four-component reaction between isoquinoline, ethyl bromoacetate, o-hydroxybenzaldehyde and nitromethane. This methodology was further extended to the synthesis of lamellarin D trimethyl ether and a formal synthesis of lamellarin D. The controlled demethylation of lamellarin D trimethyl ether yielded dihydroxy and tetrahydroxy lamellarin analogues regioselectively.

引用

页数：7

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