Concise Enantioselective Total Synthesis of Isopavine Alkaloids

被引：5

作者：

Pu, Liu-Yang ^{[1
,2
]}

Li, Zhiyue ^{[1
,2
]}

Li, Limin ^{[1
,2
]}

Ma, Yucui ^{[1
,2
]}

Hu, Shengquan ^{[1
,2
]}

Wu, Zhengzhi ^{[1
,2
]}

机构：

[1] Shenzhen Univ, Shenzhen Peoples Hosp 2, Affiliated Hosp 1, Shenzhen Inst Translat Med, Shenzhen 518035, Peoples R China

[2] Shenzhen Inst Geriatr, Shenzhen 518035, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 07期

关键词：

ASYMMETRIC-SYNTHESIS; SECONDARY ALCOHOLS; HYDROGENATION; OXIDATION; DESIGN; PAVINE;

D O I：

10.1021/acs.joc.2c02899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a concise asymmetric total synthesis of isopavine alkaloids, which feature a special azabicyclo[3.2.2]nonane tetracyclic skeleton. The key steps include iridium-catalyzed asymmetric hydrogenation of unsaturated carboxylic acids, Curtius rearrangement, and Eschweiler-Clarke methylation, which enable an enantioselective approach to isopavine alkaloids in 6-7 linear steps. Furthermore, for the first time, isopavine alkaloids, especially (-)-reframidine (3), are found to display effective antiproliferative effects on various cancer cell lines.

引用

页码：4317 / 4324

页数：8

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