Annulation of O-silyl N,O-ketene acetals with alkynes for the synthesis of dihydropyridinones and its application in concise total synthesis of phenanthroindolizidine alkaloids

被引：1

作者：

Lee, Seokwoo ^{[1
,2
]}

Shin, Jae Eui ^{[1
]}

Yoon, Ran ^{[1
]}

Yoo, Hanbin ^{[1
]}

Kim, Sanghee ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Pharm, Seoul, South Korea

[2] Chungnam Natl Univ, Coll Pharm, Daejeon, South Korea

来源：

FRONTIERS IN CHEMISTRY | 2023年 / 11卷

基金：

新加坡国家研究基金会;

关键词：

N-heterocycle; O-silyl; N; O-ketene acetal; dihydropyridinone; total synthesis; phenanthroindolizidine; phenanthroquinolizidine; alkaloid; CONIA-ENE; AMIDES; DERIVATIVES; ARYLATION; ACCESS;

D O I：

10.3389/fchem.2023.1267422

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The formation of N-heterocycles with multiple substituents is important in organic synthesis. Herein, we report a novel method for the construction of functionalized dihydropyridinone rings through the annulation of an amide alpha-carbon with a tethered alkyne moiety. The reaction of the amide with the alkyne was achieved via O-silyl N,O-ketene acetal formation and silver-mediated addition. Furthermore, the developed method was applied for the total synthesis of phenanthroindolizidine and phenanthroquinolizidine alkaloids. By varying the coupling partners, a concise and collective total synthesis of these alkaloids was achieved.

引用

页数：6

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