Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides

An efficient route to synthesize chiral carbocyclic pyrimidine nucleoside analogues containing all-carbon quaternary stereocenters has been established via the asymmetric intermolecular cyclopropanation of N1-vinylpyrimidines and aaryl diazoesters. With 2 mol% of chiral dirhodium (II) carboxylate complex as the catalyst, a variety of chiral carbocyclic cytosine or uracil nucleoside analogues were obtained in good yields (up to 96% yield), high diastereoselectivities (> 20:1 dr), and excellent enantioselectivities (up to 99% ee).

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Construction of All‐Carbon Quaternary Stereocenters via Asymmetric Cyclopropanations: Synthesis of Chiral Carbocyclic Pyrimidine Nucleosides

Wang

Guan

Xie

et al. 2018

Adv Synth Catal

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Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides.

Hong

2006

ChemInform

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Nucleic acids U 0700Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides. -Novel phenyl-branched cyclopropyl nucleosides [cf. (VII)] as well as related phosphonate and phosphonic acid nucleosides [cf. (X)] are synthesized and evaluated for their antiviral effects. None of the products exhibit good antiviral activity. Compound (Xb) possesses moderate anti-HCMV activity. -(OH, C. H.; HONG*, J. H.; Arch. Pharm. (Weinheim, Ger.) 339 (2006) 9, 507-512; Coll. Pharm., Chosun Univ., Gwangju 501-759, S. Korea; Eng.) -R. Langenstrassen 52-210

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Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain

Koszytkowska‐Stawińska

Clercq

Balzarini

2009

Bioorganic & Medicinal Chemistry

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Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides

Cited by 7 publications

References 13 publications

Construction of All‐Carbon Quaternary Stereocenters via Asymmetric Cyclopropanations: Synthesis of Chiral Carbocyclic Pyrimidine Nucleosides

Construction of All‐Carbon Quaternary Stereocenters via Asymmetric Cyclopropanations: Synthesis of Chiral Carbocyclic Pyrimidine Nucleosides

Synthesis and Antiviral Evaluation of Novel Cyclopropyl Nucleosides, Phosphonate Nucleosides and Phosphonic Acid Nucleosides.

Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain

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