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Volumn 30, Issue 6, 2011, Pages 391-404

Synthesis of cyclobutane nucleosides

Author keywords

Carbocyclic nucleosides; cyclobutane nucleosides; cyclobutanone

Indexed keywords

2 (6 AMINO PURIN 7 YL) 3 HYDROXYMETHYL CYCLOBUTANOL; 2 (6 AMINO PURIN 9 YL) 3 HYDROXYMETHYL CYCLOBUTANOL; 7 (2 HYDROXY 4 HYDROXYMETHYL CYCLOBUTYL) 1,7 DIHYDRO PURIN 6 ONE; ALCOHOL; AMMONIA; AMMONIUM HYDROXIDE; BENZOIC ACID; CYCLOBUTANE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79960989906     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2011.584513     Document Type: Article
Times cited : (10)

References (26)
  • 1
    • 54949098894 scopus 로고    scopus 로고
    • Nucleoside analogs: Molecular mechanisms signaling cell death
    • Ewald, B.; Sampath, D.; Plunkett, W. Nucleoside analogs: molecular mechanisms signaling cell death. Oncogene 2008, 27, 6522-6537.
    • (2008) Oncogene , vol.27 , pp. 6522-6537
    • Ewald, B.1    Sampath, D.2    Plunkett, W.3
  • 4
    • 33745920219 scopus 로고    scopus 로고
    • Total synthesis of dapiramicin B
    • DOI 10.1016/j.tetlet.2006.06.001, PII S0040403906011403
    • Ohno, H.; Terui, T.; Kitawaki, T.; Chida, N. Total synthesis of dapiramicin B. Tetrahedron Letters 2006, 47, 5747-5750. (Pubitemid 44040886)
    • (2006) Tetrahedron Letters , vol.47 , Issue.32 , pp. 5747-5750
    • Ohno, H.1    Terui, T.2    Kitawaki, T.3    Chida, N.4
  • 6
    • 0023377503 scopus 로고
    • Inhibition of infectivity of human immunodeficiency virus by oxetanocin
    • a) Hoshino, H.; Shimizu, N.; Shimada, N.; Takita, T.; Takeuchi, T. Inhibition of infectivity of human immunodeficiency virus by oxetanocin. J. Antibiot. 1987, 40, 1077-1078
    • (1987) J. Antibiot. , vol.40 , pp. 1077-1078
    • Hoshino, H.1    Shimizu, N.2    Shimada, N.3    Takita, T.4    Takeuchi, T.5
  • 7
    • 34547174711 scopus 로고    scopus 로고
    • Stereoselective route to oxetanocin carbocyclic analogs based on a [2+2] photocycloaddition to a chiral 2(5H)-furanone
    • For additional references to this and related compounds, see
    • b) For additional references to this and related compounds, see: Rustullet, A.; Alibés, R.; de March, P.; Figueredo, M.; Font, J. Stereoselective route to oxetanocin carbocyclic analogs based on a [2+2] photocycloaddition to a chiral 2(5H)-furanone. Org. Lett. 2007, 9, 2827-2830.
    • (2007) Org. Lett. , vol.9 , pp. 2827-2830
    • Rustullet, A.1    Alibés, R.2    De March, P.3    Figueredo, M.4    Font, J.5
  • 9
    • 0029052190 scopus 로고
    • Regioselective Coupling of tetraalkylammonium salts of 6-iodo-2-aminopurine to a cyclobutyl triflate: Efficient preparation of homochiral BMS-180 194, a potent antiviral carbocyclic nucleoside
    • b) Bisacchi, G.S.; Singh, J.; Godfrey, J.D., Jr.; Kissick, T.P.; Mitt, T.; Malley, M. F.; Marco, J.D.; Gougoutas, J.Z.; Mueller, R.H.; Zahler, R. Regioselective Coupling of tetraalkylammonium salts of 6-iodo-2-aminopurine to a cyclobutyl triflate: efficient preparation of homochiral BMS-180,194, a potent antiviral carbocyclic nucleoside. J. Org. Chem. 1995, 60, 2902-2905
    • (1995) J. Org. Chem. , Issue.60 , pp. 2902-2905
    • Bisacchi, G.S.1    Singh, J.2    Godfrey Jr., J.D.3    Kissick, T.P.4    Mitt, T.5    Malley, M.F.6    Marco, J.D.7    Gougoutas, J.Z.8    Mueller, R.H.9    Zahler, R.10
  • 11
    • 0034491961 scopus 로고    scopus 로고
    • Antiviral efficacy of lobucavir (BMS-180194), a cyclobutyl-guanosine nucleoside analogue, in the woodchuck (Marmota monax) model of chronic hepatitis B virus (HBV) infection
    • DOI 10.1016/S0166-3542(00)00128-5, PII S0166354200001285
    • d) Genovesi, E.V.; Lamb, L.; Medina, I.; Taylor, D.; Seifer, M.; Innaimo, S.; Colonno, R.J.; Clark, J.M. Antiviral efficacy of lobucavir (BMS-180194), a cyclobutyl-guanosine nucleoside analogue, in the woodchuck (Marmota monax) model of chronic hepatitis B virus (HBV) infection. Anti ViralRes. 2000,48,197-203 (Pubitemid 32112613)
    • (2000) Antiviral Research , vol.48 , Issue.3 , pp. 197-203
    • Genovesi, E.V.1    Lamb, L.2    Medina, I.3    Taylor, D.4    Seifer, M.5    Innaimo, S.6    Colonno, R.J.7    Clark, J.M.8
  • 13
    • 43549090706 scopus 로고    scopus 로고
    • Expedient approach to chiral cyclobutanones: Asymmetric synthesis of cyclobut-G
    • f) Darses, B.; Greene, A.E.; Coote, S.C.; Poisson, J.-F. Expedient approach to chiral cyclobutanones: asymmetric synthesis of cyclobut-G. Org. Lett. 2008, 10, 821-824.
    • (2008) Org. Lett. , vol.10 , pp. 821-824
    • Darses, B.1    Greene, A.E.2    Coote, S.C.3    Poisson, J.-F.4
  • 14
    • 45849096108 scopus 로고    scopus 로고
    • Bicyclic nucleoside synthesis - A photochemical approach
    • DOI 10.1080/15257770802088886, PII 794280231
    • a) Lee-Ruff, E.; Wells, D. Bicyclic nucleoside synthesis-a photochemical approach. Nucleosides, Nu-cleotides Nucleic Acids 2008, 27, 484-494 (Pubitemid 351878533)
    • (2008) Nucleosides, Nucleotides and Nucleic Acids , vol.27 , Issue.5 , pp. 484-494
    • Lee-Ruff, E.1    Wells, D.2
  • 15
    • 33947144705 scopus 로고    scopus 로고
    • Cyclobutanone photoadducts of HCN and malononitrile: useful intermediates for the synthesis of C-nucleosides
    • DOI 10.1016/j.tetlet.2007.02.046, PII S0040403907002973
    • b) Mladenova, G.; Lee-Ruff, E. Cyclobutanone photoadducts of HCN and malononitrile: useful intermediates for the synthesis of C-nucleosides. Tetrahedron Lett. 2007, 48, 2787-2789 (Pubitemid 46400790)
    • (2007) Tetrahedron Letters , vol.48 , Issue.15 , pp. 2787-2789
    • Mladenova, G.1    Lee-Ruff, E.2
  • 16
    • 27844498689 scopus 로고    scopus 로고
    • Synthesis of fluorocyclobutanones and their use in the synthesis of fluoronucleosides
    • DOI 10.1016/j.jfluchem.2005.09.007, PII S0022113905002575
    • c) Ghazi, H.; Lee-Ruff, E. Synthesis of fluorocyclobutanones and their use in the synthesis of fluoronucleosides. J. Fluor. Chem. 2005, 126, 1565-1569 (Pubitemid 41642724)
    • (2005) Journal of Fluorine Chemistry , vol.126 , Issue.11-12 , pp. 1565-1569
    • Ghazi, H.1    Lee-Ruff, E.2
  • 17
    • 0037069704 scopus 로고    scopus 로고
    • Photochemistry on soluble polymer supports: Synthesis of nucleosides
    • d) Zhong,J.-H.; Fishman, A.; Lee-Ruff, E. Photochemistry on soluble polymer supports: synthesis of nucleosides. Org. Lett. 2002, 4, 4415-4417
    • (2002) Org. Lett. , vol.4 , pp. 4415-4417
    • Zhong, J.-H.1    Fishman, A.2    Lee-Ruff, E.3
  • 18
    • 0028321959 scopus 로고
    • A novel approach toward the synthesis of chiral 2,3-dideoxy nucleosides and their carbocyclic analogues
    • DOI 10.1021/jo00087a029
    • e) Lee-Ruff, E.; Wan, W-Q.; Jiang, J.-L. A novel approach toward the synthesis of chiral 2,3-dideoxy nucleosides and their carbocyclic analogs. J. Org. Chem. 1994, 59, 2114-18 (Pubitemid 24178651)
    • (1994) Journal of Organic Chemistry , vol.59 , Issue.8 , pp. 2114-2118
    • Lee-Ruff, E.1    Wan, W.-Q.2    Jiang, J.-L.3
  • 19
    • 0029976296 scopus 로고    scopus 로고
    • Enantioselective preparation of 2',3'-dideoxynucleosides and their analogs from ring-expansion of cyclobutanones. 2. synthesis of 2',3'-dideoxyribosides and (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane
    • f) Lee-Ruff, E.; Xi, F.; Qie,J.H., Enantioselective preparation of 2',3'-dideoxynucleosides and their analogs from ring-expansion of cyclobutanones. 2. synthesis of 2',3'-dideoxyribosides and (1S,3R)-1-amino-3- (hydroxymethyl)cyclopentane. J. Org. Chem. 1996, 61,1547-50
    • (1996) J. Org. Chem. , vol.61 , pp. 1547-50
    • Lee-Ruff, E.1    Xi, F.2    Qie, J.H.3
  • 21
    • 0035022789 scopus 로고    scopus 로고
    • Photochemical synthesis of novel dideoxynucleosides
    • DOI 10.1081/NCN-100002080
    • h) Lee-Ruff, E.; Margau, R. Photochemical synthesis of novel dideoxynucleosides. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 185-196. (Pubitemid 32436261)
    • (2001) Nucleosides, Nucleotides and Nucleic Acids , vol.20 , Issue.3 , pp. 185-196
    • Lee-Ruff, E.1    Margau, R.2
  • 22
    • 0035054039 scopus 로고    scopus 로고
    • Photochemical preparation of cyclopropanes from cyclobutanones
    • DOI 10.1139/cjc-79-2-114
    • Ramnauth, J.; Lee-Ruff, E. Photochemical preparation of cyclopropanes from cyclobutanones. Can. J. Chem. 2001, 79, 114-120. (Pubitemid 32323895)
    • (2001) Canadian Journal of Chemistry , vol.79 , Issue.2 , pp. 114-120
    • Ramnauth, J.1    Lee-Ruff, E.2
  • 23
    • 77954294789 scopus 로고    scopus 로고
    • Photochemical synthesis of nucleoside analogues from cyclobu¬tanones: Bicyclic and isonucleosides
    • Jaffer, M.; Ebead, A.; Lee-Ruff, E. Photochemical synthesis of nucleoside analogues from cyclobu¬tanones: bicyclic and isonucleosides. Molecules 2010, 15, 3816-3828.
    • (2010) Molecules , vol.15 , pp. 3816-3828
    • Jaffer, M.1    Ebead, A.2    Lee-Ruff, E.3
  • 24
    • 84962448802 scopus 로고    scopus 로고
    • Theoretical calculations and vibrational study of hypoxanthine in aqueous solution
    • DOI 10.1016/j.molstruc.2004.10.092, PII S0022286004008683
    • Fernandez-Quejo, M.; de la Fuente, M.; Navarro, R., Theoretical calculations and vibrational study of hypoxanthine in aqueous solution. J. Mol. Struct. 2005, 744-747, 749-757. (Pubitemid 40717436)
    • (2005) Journal of Molecular Structure , vol.744-747 , Issue.SPEC. ISS. , pp. 749-757
    • Fernandez-Quejo, M.1    De La Fuente, M.2    Navarro, R.3
  • 25
    • 77956920954 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of α-D-20,30-didehydro-20,30- dideoxy-30-C-hydroxymethyl nucleosides
    • a) Yamada, K.; Hayakawa, H.; Sakata, S.; Ashida, N.; Yoshimura, Y Synthesis and antiviral evaluation of α-D-20,30-didehydro-20,30-dideoxy- 30-C-hydroxymethyl nucleosides. Bioorganic & Medicinal Chem¬istry Letters, 2010, 20, 6013-6016
    • (2010) Bioorganic & Medicinal Chem¬istry Letters , vol.20 , pp. 6013-6016
    • Yamada, K.1    Hayakawa, H.2    Sakata, S.3    Ashida, N.4    Yoshimura, Y.5
  • 26
    • 0034741092 scopus 로고    scopus 로고
    • H NMR conformational study of a variety of α-anomers of C5-substituted 2'-deoxyuridines: Com¬parison to their antiherpetic β counterparts
    • and references therein
    • b) Poznanski, J.; Felczak, K.; Bretner, M.; Kulikowski, T.; Remin, M. H NMR conformational study of a variety of α-anomers of C5-substituted 2'-deoxyuridines: com¬parison to their antiherpetic β counterparts. Biochem. Biophys. Res. Comm. 2001, 283, 1142-1149 and references therein.
    • (2001) Biochem. Biophys. Res. Comm. , vol.283 , pp. 1142-1149
    • Poznanski, J.1    Felczak, K.2    Bretner, M.3    Kulikowski, T.4    Remin, M.5


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