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
收藏
页码：7149 / 7153
页数：5
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