IBX-mediated oxidative addition of isocyanides to cyclic secondary amines: total syntheses of alangiobussine and alangiobussinine

被引：22

作者：

Ambule, Mayur D. ^{[1
,2
]}

Tripathi, Shashank ^{[1
,2
]}

Ghoshal, Anirban ^{[1
,2
]}

Srivastava, Ajay K. ^{[1
,2
]}

机构：

[1] Cent Drug Res Inst, CSIR, Div Med & Proc Chem, Sect 10, Lucknow 226031, Uttar Pradesh, India

[2] Acad Sci & Innovat Res AcSIR, Chem Sci Div, New Delhi 110025, India

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 73期

关键词：

UGI-TYPE; DIRECT FUNCTIONALIZATION; DIVERSITY; ALKALOIDS; REAGENT; AMIDES;

D O I：

10.1039/c9cc05215a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The present study describes a robust and general method for the synthesis of C(1)-carboxamides through IBX-mediated oxidative addition of isocyanides to tryptolines and 1,2,3,4-tetrahydroisoquinolines. In this transformation, IBX plays a dual role of an oxidant and Lewis acid to activate imine facilitating isocyanide addition. Detailed mechanistic investigations were performed by isotopic labeling and real-time NMR experiments. The method was utilized for the gram scale syntheses of two alkaloids alangiobussine and alangiobussinine in 63% and 45% overall yield, respectively.

引用

页码：10872 / 10875

页数：4

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