Advanced search
Publication Cover
Nucleosides, Nucleotides & Nucleic Acids Volume 38, 2019 - Issue 6
Submit an article Journal homepage
192
Views
2
CrossRef citations to date
0
Altmetric
Articles

Rhodium catalyzed stereospecific reductive carbocyclization of 1,6-enynes and synthesis of 4′-methyl-6′-substituted aristeromycins

Ramakrishnamraju SamunuriChemistry Services, GVK Biosciences Pvt.Ltd, Hyderabad, Telangana, India; ;Department of Chemistry, Birla Institute of Technology, Ranchi, Jharkhand, India
,
Ashok Kumar JhaChemistry Services, GVK Biosciences Pvt.Ltd, Hyderabad, Telangana, India; Correspondence[email protected] [email protected]
&
Chandralata BalDepartment of Chemistry, Birla Institute of Technology, Ranchi, Jharkhand, IndiaCorrespondence[email protected] [email protected]
Pages 391-399 | Received 11 Feb 2018, Accepted 20 Nov 2018, Published online: 28 Jan 2019

References

  • Yuen, M.-F.; Ahn, S. H.; Chen, D.-S.; Chen, P.-J.; Dusheiko, G. M.; Hou, J.-L.; Maddrey, W. C.; Mizokami, M.; Seto, W.-K.; Zoulim, F.; Lai, C.-L. Chronic Hepatitis B Virus Infection: Disease Revisit and Management Recommendations. J. Clin. Gastroenterol. 2016, 50, 286–294. DOI: 10.1097/MCG.0000000000000478.
  • Liu, J.; Goicochea, P.; Block, T.; Brosgart, C. L.; Donaldson, E. F.; Lenz, O.; Gee Lim, S.; Marins, E. G.; Mishra, P.; Peters, M. G.; Miller, V. Advancing the Regulatory Path on Hepatitis B Virus Treatment and Curative Research: a Stakeholders Consultation. J. Virus Eradic. 2017, 3, 1–6.
  • Innaimo, S. F.; Seifer, M.; Bisacchi, G. S.; Standring, D. N.; Zahler, R.; Colonno, R. J. Identification of BMS-200475 as a Potent and Selective Inhibitor of Hepatitis B Virus. Antimicrob. agents Chemother. 1997, 41, 1444–1448. DOI: 10.1128/AAC.41.7.1444.
  • Kumamoto, H.; Fukano, M.; Nakano, T.; Iwagami, K.; Takeyama, C.; Kohgo, S.; Imoto, S.; Amano, M.; Kuwata-Higashi, N.; Aoki, M.; et al. Diastereoselective Synthesis of 6 ″-(Z)-and 6 ″-(E)- Fluoro Analogues of anti-hepatitis B Virus Agent Entecavir and Its Evaluation of the Activity and Toxicity Profile of the Diastereomers. J. Org. Chem. 2016, 81, 2827–2836. DOI: 10.1021/acs.joc.6b00105.
  • Kumamoto, H.; Fukano, M.; Imoto, S.; Kohgo, S.; Odanaka, Y.; Amano, M.; Kuwata-Higashi, N.; Mitsuya, H.; Haraguchi, K.; Fukuhara, K. A Novel Entecavir Analogue Constructing with a Spiro [2.4] heptane Core Structure in the Aglycon Moiety: Its Synthesis and Evaluation for anti- hepatitis B Virus Activity. Nucleos. Nucl. Nucleic Acids. 2017, 30, 1–11.
  • Rawal, R. K.; Bariwal, J.; Singh, V. Chemistry and Bioactivities of Aristeromycins: An Overview. Curr. top. med. Chem. 2016, 16, 3258–3273.
  • Betson, M.; Allanson, N.; Wainwright, P. A Review of Methods to Synthesise 4'-substituted nucleosides. Org. Biomol. Chem. 2014, 12, 9291–9306.
  • Kato, K.; Suzuki, H.; Tanaka, H.; Miyasaka, T. Enantio- and Diastereoselective Synthesis of 4′-α-Substituted Carbocyclic Nucleosides. Tetrahedron: Asymmetr. 1998, 9,911–914. DOI: 10.1016/S0957-4166(98)00065-2.
  • Gumina, G.; Chong, Y.; Choi, Y.; Chu, C. K. Stereoselective Synthesis of Carbocyclic L-4'-fluoro-2',3'-dideoxyadenosine. Org. Lett. 2000, 2, 1229–1231.
  • Jang, H.-Y.; Krische, M. J. Rhodium-Catalyzed Reductive Cyclization of 1, 6-Diynes and 1, 6- Enynes Mediated by Hydrogen: Catalytic C − C Bond Formation via Capture of Hydrogenation Intermediates. J. Am. Chem. Soc. 2004, 126, 7875–7880. DOI: 10.1021/ja048498i.
  • Thiyagarajan, A.; Salim, M. T.; Balaraju, T.; Bal, C.; Baba, M.; Sharon, A. Structure Based Medicinal Chemistry Approach to Develop 4-methyl-7-deazaadenine Carbocyclic Nucleosides as anti-HCV Agent. Bioorg. Med. Chem. Lett. 2012, 22, 7742–7747. DOI: 10.1016/j.bmcl.2012.09.072.
  • Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. Reaction of Ethynylmagnesium Bromide with 2, 3-O-Isopropylidene-D-ribose and 2, 3: 5, 6-di-O-isopropylidene-D-mannofuranose: Syntheses of Glycofuranosylethynes. Carbohydr. Res. 1974, 36, C5–C7. DOI: 10.1016/S0008-6215(00)82020-0.
  • Buchanan, J. G.; Dunn, A. D.; Edgar, A. R. C-nucleoside Studies. Part II. Pentofuranosylethynes From 2, 3-O-isopropylidene-D-Ribose. J. Chem. Soc, Perkin Trans. 1975, 1,1191–1200. DOI: 10.1039/p19750001191.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.