A Substrate-Directed Diastereoselective Synthesis of Vicinal Diamines Using an A3-Coupling Strategy: An Application to the Total Synthesis of (+)- and (-)-Epiquinamides

被引：8

作者：

Ajay, Sama ^{[1
]}

Saidhareddy, Puli ^{[1
]}

Shaw, Arun K. ^{[1
]}

机构：

[1] CSIR, CDRI, Med & Proc Chem Div, Sector 10, Lucknow 226031, UP, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 05期

关键词：

A(3) coupling; alkaloids; alpha-amino aldehydes; epiquinamide; total synthesis; ENANTIOSELECTIVE SYNTHESIS; STEREOCONTROLLED SYNTHESIS; NATURAL-PRODUCTS; (+)-EPIQUINAMIDE; AMINES; EPIQUINAMIDE; DERIVATIVES; BETA; ACCESS; PIPERAZIN-2-ONES;

D O I：

10.1002/ajoc.201700049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed highly diastereoselective multicomponent reaction (MCR) of alpha-amino aldehydes, dibenzylamine and various alkynes leading to propargyl syn 1,2-diamines has been established. The methodology has been further supported by the total synthesis of (+)- and (-)-epiquinamides from A(3)-coupled adducts derived from L- and D-pipecolic acids, respectively, in overall yields of 31%.

引用

页码：503 / 506

页数：4

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