An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine

被引：10

作者：

Li, Jihui ^{[1
]}

Liu, Yongxiang ^{[1
,2
,3
]}

Song, Xinjing ^{[1
]}

Wu, Tianxiao ^{[1
]}

Meng, Jiaxin ^{[1
]}

Zheng, Yang ^{[1
]}

Qin, Qiaohua ^{[1
]}

Zhao, Dongmei ^{[1
]}

Cheng, Maosheng ^{[1
,3
]}

机构：

[1] Shenyang Pharmaceut Univ, Minist Educ, Key Lab Struct Based Drug Design & Discovery, Shenyang 110016, Liaoning, Peoples R China

[2] Shenyang Pharmaceut Univ, Wuya Coll Innovat, Shenyang 110016, Liaoning, Peoples R China

[3] Inst Drug Res Med Capital China, Benxi 117000, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; PROTOBERBERINE ALKALOIDS; PHTHALIDEISOQUINOLINE; NOSCAPINE; DEPROTECTION; ALKYLATION; ANTAGONIST; MECHANISM; AGENT; CELLS;

D O I：

10.1021/acs.orglett.9b02715

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (+/-)-beta-Noscapine and (+/-)-beta-Hydrastine were exploited.

引用

页码：7149 / 7153

页数：5

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