Abstract:
The readily available Corey lactone was converted in three simple stages to tris-TBS-ether of (1R*,3R*,5S*)-1-hydroxymethyl-3,5-dihydroxy-2-methylidenecyclopentane – the protected carbocyclic core of Entecavir, one of the best medicines against hepatitis.
Document Type:
Article
Language: English
Citation:
Z. R. Valiullina, V. A. Akhmet'yanova, N. S. Vostrikov, M. S. Miftakhov, “A short synthesis of the carbocyclic core of Entecavir from Corey lactone”, Mendeleev Commun., 26:1 (2016), 9–10
Linking options:
https://www.mathnet.ru/eng/mendc2091
https://www.mathnet.ru/eng/mendc/v26/i1/p9
This publication is cited in the following 6 articles:
Guo-Tai Zhang, Gen Li, Linxi Wan, Xinxin Pu, Junhai Chang, Pei Tang, Fen-Er Chen, “Asymmetric Total Synthesis of Anti-HBV Drug Entecavir: Catalytic Strategies for the Stereospecific Construction of Densely Substituted Cyclopentene Cores”, Org. Lett., 26:22 (2024), 4818
A. M. Gimazetdinov, V. V. Zagitov, Z. R. Makaev, N. S. Vostrikov, M. S. Miftakhov, “Some aspects of the synthesis and modification of cross-conjugated cyclopentenone prostaglandins”, Russ Chem Bull, 72:10 (2023), 2281
V. V. Loza, Z. R. Valiullina, M. S. Miftakhov, “Adducts of dichloroketene with 1,3-cyclopentadienes in the synthesis of bioactive cyclopentanoids”, Russ Chem Bull, 70:1 (2021), 1
Huiying Wang, Qiuhua Wang, Yaling Wu, Lingping Cheng, Lunan Zhu, Junchen Zhu, Yanxiong Ke, “HPLC and SFC enantioseparation of (±)‐Corey lactone diol: Impact of the amylose tris‐(3,5‐dimethylphenylcarbamate) coating amount on chiral preparation”, Chirality, 31:10 (2019), 855
T. V. Ghochikyan, M. A. Samvelyan, A. S. Galstyan, V. M. Muzalevskiy, V. G. Nenajdenko, “Copper catalyzed alkyne–azide cycloaddition with 3-propargyl- γ-butyrolactones”, Mendeleev Commun., 27:6 (2017), 562–564
N. S. Vostrikov, I. F. Lobko, Z. R. Valiullina, M. S. Miftakhov, “Synthesis of racemic Entecavir”, Mendeleev Commun., 27:1 (2017), 12–13
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