Total Syntheses of Phleghenrines A and C

被引：2
|
作者：
Cai, Xinpei [1 ,2 ]
Li, Lei [1 ,2 ,3 ]
Wang, Ye-Cheng [1 ,2 ]
Zhou, Jianhan [1 ,2 ]
Dai, Mingji [1 ,2 ,3 ]
机构：
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
[2] Purdue Univ, Ctr Canc Res, W Lafayette, IN 47907 USA
[3] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 28期
关键词：
MASKED O-BENZOQUINONES; LYCOPODIUM ALKALOIDS; EFFICIENT SYNTHESIS; LYCONADINS; HUPERZINE;
D O I：
10.1021/acs.orglett.3c01784
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the total syntheses of phleghenrinesA and Cfrom commercially available starting materials in 7 and 8 steps, respectively.Notable steps include an inverse electron-demand Diels-Alderreaction between a masked o-benzoquinone and a N-protected enamine to prepare one key intermediate witha bicyclo[2.2.2]octenone core, a Bu''chner-Curtius-Schlotterbeckone-carbon insertion to expand the bicyclo[2.2.2]octenone to a bicyclo[3.2.2]nonenone,and Trauner's modified 2-pyridone synthesis to install the2-pyridone moiety.
引用
收藏
页码：5258 / 5261
页数：4
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