Dragocins A~C的关键中间体呋喃核糖基供体的合成  

Synthesis of the key intermediate furan ribosyl donor of Dragocins A~C

作　　者：孙启凯 程国强 丁瀚 王鹏[1] 李明[1,2] SUN Qi-kai;CHENG Guo-qiang;DING Han;WANG Peng;LI Ming(Key Laboratory of Marine Drugs,Ministry of Education,School of Medicine and Pharmacy,Ocean University of China,Qingdao 266003,China;Laboratory for Marine Drugs and Bioproducts of Qingdao Pilot National Laboratory for Marine Science and Technology,Qingdao 266237,China)

机构地区：[1]中国海洋大学海洋药物教育部重点实验室,医药学院,山东青岛266003 [2]青岛海洋科学与技术试点国家实验室海洋药物与生物制品功能实验室,山东青岛266237

出　　处：《中国海洋药物》2021年第3期41-45,共5页Chinese Journal of Marine Drugs

基　　金：国家自然科学基金项目项目(21672194,21977088)资助。

摘　　要：目的对海洋蓝藻来源天然产物Dragocins A~C的关键呋喃核糖砌块进行合成研究,旨在为Dragocins A~C的合成提供有效方案,以期解决Dragocins A~C天然来源有限的问题,进而为其生物活性及作用机制研究奠定基础。方法采用去对称化策略选择性保护支链型核糖6的β面伯羟基,通过氧化7的伯羟基、水解10的丙酮叉及异头位甲氧基和活化11的异头位乙酰基生成硫苷等关键反应操作,完成目标化合物的合成。结果从已知的支链型核糖甲苷6出发,经8步反应,以39%的总收率获得了关键中间化合物4,为Dragocins A~C的全合成奠定了物质基础。Objective We operated the synthetic research on the key ribofuranose blocks of nature products Dragocins A~C from marine cyanobacteria,to provide a proven solution for the synthesis of Dragocins A~C,solve the problem of their limited natural sources and lay the foundation for their biological activity and mechanism study.Methods Selective protection ofβside hydroxymethyl group of 6,oxidization of the remaining one of 7,hydrolysis of isopropylidene ketal and anomeric methoxyl group of 10,and the following activation of anomeric acetate of 11 to provide the thioribofuranoside finished the synthesis of the target molecule.Results Starting from branched riboside 6,the key thioribofuranoside donor 4 was obtained through 8 steps in 39%yield,laying the solid foundation for the total synthesis of Dragocins A~C.

关 键 词：Dragocins AC 支链糖 核糖衍生物 

分 类 号：R914[医药卫生—药物化学]