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Organocatalytic and Scalable Synthesis of the Anti-Influenza Drugs Zanamivir, Laninamivir, and CS-8958
Alternative Title有机小分子催化合成抗流感药物Zanamivir, Laninamivir, and CS-8958
Tian JS(田俊山); Zhong JK(钟建康); Li YS(李运生); Ma DW(马大为)
2014
Source PublicationAngew. Chem.-Int. Edit.
Volume53Issue:50Pages:13885-13888
AbstractZanamivir, laninamivir, and CS-8958 are three neuraminidase inhibitors that have been clinically used to combat influenza. We report herein a novel organocatalytic route for preparing these agents. Only 13steps are needed for the assembly of zanamivir and laninamivir from inexpensive D-araboascorbic acid by this synthetic route, which relies heavily on a thiourea-catalyzed enantioselective Michael addition of acetone to tert-butyl (2-nitrovinyl)carbamate and an anti-selective Henry reaction of the resulting Michael adduct with an aldehyde prepared from D-araboascorbic acid. The synthetic procedures are scalable, as evident from the preparation of more than 3.5g of zanamivir.
Subject Area生命有机化学
DOI10.1002/anie.201408138
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Indexed BySCI
Language英语
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38966
Collection生命有机化学国家重点实验室
Corresponding AuthorMa DW(马大为)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
Tian JS,Zhong JK,Li YS,et al. Organocatalytic and Scalable Synthesis of the Anti-Influenza Drugs Zanamivir, Laninamivir, and CS-8958[J]. Angew. Chem.-Int. Edit.,2014,53(50):13885-13888.
APA 田俊山,钟建康,李运生,&马大为.(2014).Organocatalytic and Scalable Synthesis of the Anti-Influenza Drugs Zanamivir, Laninamivir, and CS-8958.Angew. Chem.-Int. Edit.,53(50),13885-13888.
MLA 田俊山,et al."Organocatalytic and Scalable Synthesis of the Anti-Influenza Drugs Zanamivir, Laninamivir, and CS-8958".Angew. Chem.-Int. Edit. 53.50(2014):13885-13888.
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