Practical synthesis of immucillins BCX-1777 and BCX-4430

Minjie Zhang; Fei Xue; Jingdan Ou; Yuan Huang; Fei Lu; Bingqing Zhou; Zhibing Zheng; Xiao-Yu Liu; Wu Zhong; Yong Qin

doi:10.1039/D0QO01026J

Practical synthesis of immucillins BCX-1777 and BCX-4430†

Minjie Zhang,‡^a Fei Xue,‡^a Jingdan Ou,^a Yuan Huang,^a Fei Lu,^a Bingqing Zhou,^a Zhibing Zheng,^b Xiao-Yu Liu,^a Wu Zhong*^b and Yong Qin

*^a

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^a Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, Sichuan Province, China
E-mail: yongqin@scu.edu.cn

^b National Engineering Research Center for the Emergence Drugs, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China
E-mail: zhongwu@bmi.ac.cn

Abstract

A practical synthesis of immucillins BCX-1777 and BCX-4430 is disclosed. Highlights of the synthesis include the addition of lithiated 9-deazapurine derivative 10 to the stable tri-O-benzyl cyclic nitrone 13 to form the imino-C-nucleoside skeleton, and an efficient copper-catalysed Ullmann-type amination to install the amino group on the heterocyclic moiety of BCX-4430.

Organic Chemistry Frontiers

Practical synthesis of immucillins BCX-1777 and BCX-4430†

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Practical synthesis of immucillins BCX-1777 and BCX-4430

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