Chiral Synthesis of Antiviral Nucleosides from Carbohydrate Templates

Antiviral Nucleosides: Chiral Synthesis and Chemotherapy

Volumn , Issue , 2003, Pages 77-189

  Gumina, Giuseppe ^a   Olgen, Sureyya ^a   Chu, Chung K ^a  

^a NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84942124045     PISSN: None     EISSN: None     Source Type: Journal    
DOI: 10.1016/B978-044451319-9/50002-6     Document Type: Chapter

References (240)

1. Gumina G., Song G.-Y., Chu C.K. l-Nucleosides as chemotherapeutic agents. FEMS Microbiol. Lett. 2001, 202:9-15.
2. Gumina G., Song G.-Y., Chu C.K. Advances in antiviral agents for hepatitis B virus. Antiviral Chem. Chemother. 2001, 12:89-112.
3. Cooperwood J.S., Gumina G., Boudinot F.D., Chu C.K. Nucleoside and nucleotide prodrugs. Recent Advances in Nucleosides: Chemistry and Chemotherapy 2002, 91-147. C.K. Chu (Ed.).
4. Kinchington D. Recent advances in antiviral therapy. J. Clin. Pathol. 1999, 52:89-94.
5. Mansour T.S., Storer R. Antiviral nucleosides. Curr. Pharm. Design 1997, 3:227-264.
6. De Clercq E. HIV inhibitors targeted at the reverse transcriptase. AIDS Res. Hum. Retroviruses 1992, 8:119-134.
7. Schinazi R.F., Mead J.R., Feorino P.M. Insighi into HIV chemotherapy. AIDS Res. Hum. Retroviruses 1992, 8:963-990.
8. De Clercq E. Antiviral activity spectrum and target of action of different classes of nucleoside analogs. Nucleosides Nucleotides 1994, 13:1271-1295.
9. Reist E.J., Goodman L., Lee W.W., Baker B.R., Benitez A. Potential anticancer agents. 76. Synthesis of purine nucleosides of β-d-arabinofuranose. J. Org. Chem. 1962, 27:3274-3279.
10. Parks R., Stoeckler J., Cambor C., Savarese T., Crabtree G., Chu S. Molecular actions and targets for cancer chemotherapeutic agents 1981, 229. Academic Press, New York. A. Sartorelli, T. Lazo, J. Bertino (Eds.).
11. Paulsen H., Todt K. Adv. Carbohydr. Chem. 1968, 23:115-232.
12. Dyson M.R., Coe P.L., Walker R.T. An improved synthesis of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-d-eryhtro-pentofuranoside, an intermediate in the synthesis of 4'-thionucleosides. Carbohyd. Res. 1991, 216:237-248.
13. Bredenkamp M.W., Holzapfel C.W., Swanepoel A.D. Stannylene directed selective acylation of some open-chain-arabinose derivatives. Tetrahedron Lett. 1990, 31:2759-2762.
14. Bellon L., Barascut J.L., Imbach J.L. Efficient synthesis of 4-thio-d-ribofuranose and some 4'-thioribonucleosides. Nucleosides Nucleotides 1992, 11:1467-1479.
15. Classon B., Garegg P.J., Samuelsson B., Liu Z.C. Novel route to 4-thiofuranosides - synthesis of methyl 4-thioα-d-talofuranosides. J. Carbohydr. Chem. 1987, 6:593-597.
16. Huang B., Hui Y. A facile synthesis of 4'-thio-2'-deoxypyrimidine nucleosides and preliminary studies on their properties. Nucleosides Nucleotides 1993, 12:139-147.
17. Tiwari K.N., Montgomery J.A., Secrist J.A. The synthesis and biological-activity of 1-(2-deoxy-4-thioα-l-threo-pentofuranosyl)thymine. Nucleosides Nucleotides 1993, 12:841-846.
18. Dyson M.R., Coe P.L., Walker R.T. The synthesis and antiviral properties of E-5-(2-bromovinyl)-4'-thio-2'-deoxyuridine. J. Chem. Soc., Chem. Commun. 1991, 741-742.
19. Dyson M.R., Coe P.L., Walker R.T. The synthesis and antiviral activity of some 4'-thio-2'-deoxy nucleoside analogs. J. Med. Chem. 1991, 34:2782-2786.
20. Secrist J.A., Tiwari K.N., Riodan J.M., Montgomery J.A. Synthesis and biological activity of 2'-deoxy-4'-thio pyrimidine nucleosides. J. Med. Chem. 1991, 34:2361-2366.
21. Fu Y.L., Bobek M. An alternative synthesis of anomeric methyl 2-deoxy-4-thio-d-erythro-pentofuranosides. J. Org. Chem. 1976, 41:3831-3834.
22. Leydier C., Bellon L., Barascut J.L., Deydier J., Georges M., Helene P., Moulay A.E., Imbach J.L. A new synthesis of some 4'-thio-d-ribonucleosides and preliminary enzymatic evaluation. Nucleosides Nucleotides 1994, 13:2035-2050.
23. Reist E.J., Gueffroy D.E., Goodman L. Synthesis of 4-thio-d- + -l-ribofuranose + corresponding adenine nucleosides. J. Am. Chem. Soc. 1964, 86:5658-5663.
24. Bobek M., Whistler R.L., Bloch A. Synthesis and biological activity of 4'-thio analogs of the antibiotic toyocamycin. J. Med. Chem. 1972, 15:168-171.
25. Bobek M., Bloch A., Parthasaarthy R., Whistler R.L. Synthesis and biological activity of 5-fluoro-4'-thiouridine and some related nucleosides. J. Med. Chem. 1975, 18:784-787.
26. Tber B., Fahmi N., Ronco G., Villa P., Ewing D.F., Mackenzie G. An alternative strategy for the synthesis of 3'-azido-2',3'-dideoxy-4'-thionucleosides starting from d-xylose. Carbohyd. Res. 1995, 267:203-215.
27. Wong M.Y.H., Gray G.R. 2-deoxypentoses-stereoselective reduction of ketene dithioacetals. J. Am. Chem. Soc. 1978, 100:3548-3553.
28. Aitsir H., Ewing D.F., Fahmi N., Goethals G., Mackenzie G., Ronco G., Tber B., Villa P. Synthesis of 2-deoxy-4-thio-d-ribofuranose and its 3-azido analog from l-arabinose intermediates in the synthesis of 4'-thiodeoxynucleosides. Nucleosides Nucleotides 1995, 14:359-362.
29. Jandu K.S., Selwood D.L. 4'-Thionucleosides via in situ pyranose-furanose rearrangement-A short synthesis of the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine via direct coupling of a silylated pyrimidine base with a 4-thiopyranose sugar. J. Org. Chem. 1995, 60:5170-5173.
30. Tsuda Y., Kanemitsu K., Kakimoto K., Kikuchi T. Utilization of sugars in organic synthesis. 19. Trialkyltin radical used to catalyze the O, S-rearrangement of cyclic thiocarbonate-A new entry to thio-sugars. Chem. Pharm. Bull. 1987, 35:2148-2150.
31. Rassu G., Spanu P., Pinna L., Zanardi F., Casiraghi G. 2-(tert-Butyldimethylsiloxy) thiophene: Application to total synthesis of both enantiomer of 2',3'-dideoxy-4'-thiocytidine. Tetrahedron Lett. 1995, 36:1941-1944.
32. Baer E. lα-Glycerophosphoric acid-barium salt. Biochem. Prep. 1952, 2:31-38.
33. Eibl H. An improved method for the preparation of 1,2-isopropylidene-SN-glycerol. Phys. Lipids 1981, 28:1-5.
34. Hubschwerlen C. A convenient synthesis of l-(S)-glyceraldehyde acetonide from l-ascorbic acid. Synthesis 1986, 962-964.
35. Young R.J., Shaw-Ponter S., Thomson J.B., Miller J.A., Cumming J.G., Pugh A.W., Rider P. Synthesis and antiviral evaluation of enantiomeric 2',3'-dideoxy- and 2',3'-dideohydro-2',3'-dideoxy-4'-thionucleosides. Bioorg. Med. Chem. Lett. 1995, 5:2599-2604.
36. Pederson R.L., Liu K.K.C., Rutan J.F., Chen L., Wong C.-H. Enzymes in organic synthesis-synthesis of highly enantiomerically pure 1,2-epoxy aldehyde, epoxy alcohols, thirane, aziridine, and glyceraldehyde-3-phosphate. J. Org. Chem. 1990, 55:4897-4901.
37. Taguchi Y., Suhara Y. The synthesis of dihydro-2(3H)-thiophenone derivative. Bull. Chem. Soc. Jpn. 1986, 59:2321-2324.
38. Kawakami H., Ebata T., Koseki K., Matsushita H., Naoi Y., Itoh K. Stereoselectivity in the coupling reaction between 2-phenylthio-2,3-dideoxyribose and silylated pyrimidine bases. Chem. Lett. 1990, 1459-1462.
39. Choi Y., Choo H., Chong Y, Lee S., Olgen S., Schinazi R.F., Chu C.K. Synthesis and potent anti-HIV activity of l-2',3'-didehydro-2',3'-dideoxy-2'-fluoro-4'-thiocytidine. Org. Lett. 2002, 4:305-307.
40. Choi Y., Choo H., Chong Y., Lee S., Schinazi R.F., Chu C.K. Synthesis and antiviral activities of l-2',3'-didehydro-2',3'-dideoxy-2'-fluoro-4'-thionucleosides. Abstr. Papers Am. Chem. Soc. 2001, CARB 029.
41. Choo H., Chong Y., Lee S., Choi Y., Schinazi R.F., Chu C.K. Synthesis and anti-HIV activity of d-2',3'-unsaturated-2'-fluoro-4'-thionucleosides. Abstr. Papers Am. Chem. Soc. 2002, MEDI 244.
42. Chu C.K., Choi Y., Choo H., Chong Y., Lee S., Zhu W., Schinazi R.F. Synthesis and anti-HIV activity of d- and l-2',3'didehydro-2',3'-dideoxy-2'-fluoro-4'-thiocytidines. Antiviral Res. 2002, 53:A36.
43. Van Draanen N.A., Freeman G.A., Short S.A., Harvey R., Jansen R., Szczech G., Kozalka G.W. Synthesis and antiviral activity of 2'-deoxy-4'-thiopurine nucleosides. J. Med. Chem. 1996, 39:538-542.
44. Rahim S.G., Tricedi N., Bogunovic-Batchelor M.V., Hardy G.W., Mills G., Selway J.W.T., Snowden W., Littler E., Coe P.L., Basnak I., Whale R.F., Walker R.T. Synthesis and anti-herpes virus activity of 2'-deoxy-4'-thiopyrimidine nucleosides. J. Med. Chem. 1996, 39:789-795.
45. Birk C., Voss J., Wirsching J. Preparation, structural elucidation and reactions of benzyl 2-deoxy-3,5-di-O-methyl-1,4-dithio-l-threo-pentofuranoside and synthesis of the corresponding 2'-deoxy-4'-thionucleosides. Carbohydr. Res. 1997, 304:239-247.
46. Yoshimura Y., Kitano K., Yamada K., Satoh H., Watanabe M., Miura S., Sakata S., Sasaki T., Matsuda A. A novel synthesis of 2'-modified 2'-deoxy-4'-thiocytidines from d-glucose. J. Org. Chem. 1997, 62:3140-3152.
47. Yoshimura Y., Kitano K., Satoh H., Watanabe M., Miura S., Sakata S., Sasaki T., Matsuda A. A novel synthesis of new antineoplastic 2'-deoxy-2'-substituted-4'-thiocytidines. J. Org. Chem. 1996, 61:822-823.
48. Abbruzzese J.L., Grunewald R., Weeks E.A., Gravel D., Adams T., Nowak B., Mineishi S., Tarassoff P., Satterlee W., Raber M.N., Plinkett W. A phase-1 clinical, plasma, and cellular pharmacology study of gemcitabine. J. Clin. Oncol. 1991, 9:491-498.
49. Jeong L.S., Nicklaus M.C., George C., Marquez V.E. Unanticipated retention of configuration in the DAST fluorination of deoxy-4'-thiopyrimidine nucleosides with up-hydroxyl groups. Tetrahedron Lett. 1994, 35:7569-7572.
50. Hughes N.A., Kuhajda K.M., Miljkovic D.A. New syntheses of methyl 5-thioβ-d-arabinopyranoside and (+)-biotin. Carbohydr. Res. 1994, 257:299-304.
51. Machida H., Ashida N., Miura S., Endo M., Yamada K., Kitano K., Yoshimura Y., Sakata S., Ijichi O., Eizuru Y. Anti-herpesvirus activity profile of 4'-thioarabinofuranosyl purine and uracil nucleosides and activity of 1β-d-2'-fluoro-4'-thioarabinofuranosyl guanine and 2,6-diaminopurine against clinical isolates of human cytomegalovirus. Antiviral Res. 1998, 39:129-137.
52. An S.H., Bobek M. Methyl 3,4-di-O-acetyl-2-deoxy-2(R)-[1H,3H-2,4-dioxo-1-pyrimidinyl]-2-fluoroβ-d-arabinopyranoside-novel nucleosides analogs via condensation of gem-2,2-difluoromethyl glycosides with silylated heterocyclic bases. Tetrahedron Lett. 1986, 27:3219-3222.
53. Yoshimura Y., Kitano K., Watanabe M., Satoh H., Sakata S., Miura S., Ashida N., Machida H., Matsuda A. Synthesis and biological activities of 2'-modified 4'-thionucleosides. Nucleosides Nucleotides 1997, 16:1103-1106.
54. Yoshimura Y., Watanabe M., Satoh H., Ashida N., Ijichi K., Sakata S., Machida H., Matsuda A. A facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities. J. Med. Chem. 1997, 40:2177-2183.
55. Haraguchi K., Nishikawa A., Sasakura E., Tanaka H., Nakamura K.T., Miyasaka T. Electrophilic addition to 4-thio furanoid glycal: a higly stereoselective entry to 2'-deoxy-4'-thio pyrimidine nucleosides. Tetrahedron Lett. 1998, 39:3713-3716.
56. DeValette F., Barascut J.L., Imbach J.L. Synthesis and antiviral evaluation of 2'-deoxy-4'-thio-l-nucleosides and their phosphotriester derivatives bearing S-acyl-2-thioethyl bioreversible phosphate-protecting groups. Nucleosides Nucleotides 1998, 17:2289-2310.
57. Bellon L., Leydier C., Barascut J.L., Imbach J.L. A reinvestigation of the synthesis of 4'-thiopentofuranosides for further nucleosidic synthesis. Nucleosides Nucleotides 1993, 12:847-852.
58. Debernardo S., Tengi J.P., Sasso G.J., Weigele M. Clavalanine (RO 22-5417), a new clavam antibiotic from sreptomyces-clavuligerus. 4. A stereorational synthesis. J. Org. Chem. 1985, 50:3457-3462.
59. Rasmussen J.R., Slinger C.J., Kordish R.J., Newman-Evans D.D. Synthesis of deoxy sugars-deoxygenation by treatment with N, N'-thiocarbonyldiimidazole-tri-normal-butyl stannane. J. Org. Chem. 1981, 46:4843-4846.
60. Barton D.H.R., Jang D.O., Saszberenyi J.C. The invention of radical reactions. 29. Radical monodeoxygenation and dideoxygenation with silanes. Tetrahedron 1993, 49:2793-2804.
61. Vorbrüggen H., Bennua B. Nucleoside syntheses. 19. new simplified nucleoside synthesis. Tetrahedron Lett. 1978, 15:1339-1342.
62. Secrist J.A., Tiwari K.N., Shorynacy-Fowler A.T., Messini L., Riordan J., Montgomery J.A. Synthesis and biological activity of certain 4'-thio-d-arabinofuranosylpurines. J. Med. Chem. 1998, 41:3865-3871.
63. Jeong L.S., Moon H.Y., Choi Y.J., Chun M.W., Kim H.O. A short and efficient synthesis of l-thioarabino derivative: A versatile synthon for the synthesis of l-2'-deoxy-2',3'-disubstituted-4'-thionucleosides. J. Org. Chem. 1998, 63:4821-4825.
64. Blumberg A., Fuccello A., Van Es T. Intramolecular cyclization of pentose and hexose dithio-acetals. Carbohydr. Res. 1979, 70:217-232.
65. Jeong L.S., Moon H.Y., Yoo S.J., Lee S.N., Chun M.W., Lim Y.H. Ring contraction and rearrangement of 4-thiofuranose derivatives observed during DAST fluorination in the synthesis of l-2'"UP"-fluoro-4'-thiothymidine. Tetrahedron Lett. 1998, 39:5201-5204.
66. Tiwari K.N., Montgomery J.A., Secrist J.A. The synthesis and biological activity of 1-(2-deoxy-4-thioα-l-threo-pentofuranosyl)thymine. Nucleosides Nucleotides 1993, 12:841-846.
67. Montgomery J.A., Thomas H.J. Isonucleosides. 2. Purine and pyrimidine derivatives of 1,4-anhydro-2-deoxy-d-arabinitol. J. Org. Chem. 1978, 43:541-544.
68. Kjølberg O. A new method of degrading glucose to xylose and galactose to arabinose. Acta Chem. Scan. 1960, 14:1118-1123.
69. Bobek M., An S.-H., Skrincosky D., De Clerq E., Bernacki R.J. 2'-Fluorinated isonucleosides. 1. Synthesis and biological activity of some methyl 2'-deoxy-2'-fluoro-2'-pyrimidinyl-d-arabinopyranosides. J. Med. Chem. 1989, 32:799-807.
70. Huryn D.M., Sluboski B.C., Tam S.Y., Todaro L.J., Weigele M. Synthesis of iso-ddA, member of a novel class of anti-HIV agents. Tetrahedron Lett. 1989, 30:6259-6262.
71. Nair V., Nuesca Z.M. Isodideoxynucleosides: A conceptually new class of nucleoside antiviral agents. J. Am. Chem. Soc. 1992, 114:7951-7953.
72. Zintek L.B., Jeon G.S., Nair V. The synthesis of (S) and (R) enantiomers of novel hydroxymethylated isodideoxynucleosides. F 1994, 37:1853-1864.
73. Tino J.A., Clark J.M., Field A.K., Jacobs G.A., Lis K.A., Michalik T.L., McGeever-Rubin B., Slusarchyk W.A., Spergel S.H., Sundeen J.E., Tuomari A.V., Weaver E.R., Young M.G., Zahler R. Synthesis and antiviral activity of novel isonucleoside analogs. J. Med. Chem. 1993, 36:1221-1229.
74. Kira T., Kakefuda A., Shuto S., Matsuda A., Baba M., Shigeta S. Anti-herpes activities of isonucleoside analogs with variable bases at 2' position. Nucleosides Nucleotides 1995, 14:571-574.
75. Levene P.A., Raymond A.L. Derivative of monoacetone xylose. J. Biol. Chem. 1933, 102:317-330.
76. Rosenthal A., Baker D.A. New routes to branched-chain amino sugars by application of modified Wittig reaction to ketoses. Tetrahedron Lett. 1969, 397-400.
77. Rosenthal A., Sprinzl M. Branched-chain sugars via the hydroboration-oxidation of unsaturated sugar derivatives. Carbohydrate Res. 1971, 16:337-342.
78. Franchetti P., Capellacci L., Grifantini M., Messini L., Sheikha G.A., Loi A.G., Tramontano E., DeMontis A., Spiga M.G., LaColla P. Synthesis and evaluation of the anti-HIV activity of aza and deaza analogs of isoddA and their phosphates as prodrugs. J. Med. Chem. 1994, 37:3534-3541.
79. Varela O., De Fina G.M., DeLederkremer R.M. The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide stereoselective synthesis of α-anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranoside-2-uloses. Carbohydr. Res. 1987, 167:187-196.
80. Lemieux R.U. Newer developments in the conformational analysis of carbohydrates. Pure Appl. Chem. 1971, 27:527-547.
81. Hanessian S., Banoub J. Chemistry of glycosidic linkage-efficient synthesis of 1,2-trans-disaccharides. Carbohydr. Res. 1977, 53:C13-C16.
82. Herscovici J., Bessodes M., Antonakis K. Studies on sodium-borohydride reduction of unsaturated keto nucleosides-novel route to deoxy nucleosides. J. Org. Chem. 1976, 41:3827-3830.
83. Hammerschmidt F., Ohler E., Polster J.P., Zbiral E., Balzarini J., DeClercq E. A Convenient route to d-apioβ-d-furanosyl- and 2'-deoxyapioβ-d-furanosyl nucleosides. Liebigs Ann. 1995, 551-558.
84. Hammerschmidt F., Ohler E., Polster J.P., Zbiral E., Balzarini J., DeClercq E. A Convenient route to 3'-deoxyα-l- and 3'-deoxyβ-d-apionucleosides. Liebigs Ann. 1995, 559-565.
85. Purdy D.F., Zintek L.B., Nair V. Synthesis of isonucleosides related to AZT and AZU. Nucleosides Nucleotides 1994, 13:109-126.
86. Barker R., Fletcher H.G. 2,3,5-Tri-O-benzyl-d-ribosyl and -l-arabinosyl bromides. J. Org. Chem. 1961, 26:4605-4609.
87. Bennek J.A., Gray G.R. An efficient synthesis of anhydroalditols and ally C-glycosides. J. Org. Chem. 1987, 52:892-897.
88. Heath P., Mann J., Walsh E.B., Wadsworth A.H. The preparation of dioxaprostacyclin analogs from d-(-)-ribose. J. Chem. Soc. Perkin Trans. 1 1983, 2675-2679.
89. Nicotra F., Panza L., Russo G., Zuchelli L. Chemoenzymatic approaches to carbohydrate-derivative anaolgs of platelet-activating-factor. J. Org. Chem. 1992, 57:2154-2158.
90. Montgomery J.A., Thomas H.J. Isonucleosides 2. Purine and pyrimidine-derivatives of 1,4-anhydro-2-deoxy-d-arabinitol. J. Org. Chem. 1978, 43:541-544.
91. Shaw G., Warrener R.N. Purines, pyrimidines, and glyoxalines. 8. New syntheses of uracils and thymines. J. Chem. Soc. 1958, 157-161.
92. Shealy Y.F., O'Dell C.A. Acid-catalyzed cyclization of alkoxyacrylolureas to 2,4(1H,3H) pyrimidinediones. J. Heterocycl. Chem. 1976, 13:1041-1047.
93. Sochacka E., Nawrot B., Pankiewicz K.W., Watanabe K.A. Synthesis of 1-methyl-5-(3-azido-2,3-dideoxyβ-d-erythro-pentofuranosyl)uracil and 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoroβ-d-arabinofuranosyl)uracil-the C-nucleoside isostere of 3'-azido-3'-deoxythymidine and its 2'-up-fluoro analogs. J. Med. Chem. 1990, 33:1995-1999.
94. Dunkel M., Pfleiderer W. Nucleosides 52. Synthesis and properties of quinazoleine-3'-azidonucleosides. Nucleosides Nucleotides 1993, 12:125-137.
95. Kakefuda A., Shuto S., Nagahata T., Seki J., Sasaki T., Matuda A. Nucleosides and nucleotides. 132. Synthesis and biological evaluations of ring-expanded oxetanocine analogs: purine and pyrimidine analogs of 1,4-anhydro-2-deoxy-d-arabitol and 1,4-anhydro-2-deoxy-3-hydroxymethyl-d-arabitol. Tetrahedron 1994, 50:10167-10182.
96. Barker D.C., Horton D., Tindall C.G. Large-scale preparation of d-allose: observations on stereoselectivity of reduction of 1,2-5,6-di-O-isopropylideneα-d-ribo-hexofuranos-3-ulose hydrate. Carbohydrate Res. 1972, 24:192-197.
97. Acton E.M., Goerner R.N., Uh H.S., Ryan K.J., Henry D.W. Improved anti-tumor effects in 3'-branched homologs of 2'-deoxythioguanosine-synthesis and evaluation of thioguanosine nucleosides of 2,3-dideoxy-3-(hydroxymethyl)-d-erythro-pentofuranose. J. Med. Chem. 1979, 22:518-525.
98. Ohrui H., Waga T., Ueno A., Okamoto M., Horie H., Meguro H., Kabuto C. A new reaction of adenine with a 1,4-anhydroribitol having cis-orientated azide and O-tosylate: formation of a novel aziridinoadenine isonucleoside. Biosci. Biotech. Biochem. 1995, 59:1801-1803.
99. Yu H.W., Zhang L.R., Zhou J.C., Ma L.T., Zhang L.H. Studies on the synthesis and biological activities of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines. Bioorg. Med. Chem. 1996, 4:609-614.
100. Prévost N., Rouessac F. Isonucleosides by Michael addition of pyrimidine bases on 2,6-disubstituted 2H-pyran-3(3H)-ones. Tetrahedron Lett. 1997, 38:4215-4218.
101. Prévost N., Rouessac F. A novel route to pyrimidine isodideoxynucleosides via Michel-type addition on unsaturated modified sugars. Synthetic Commun. 1997, 27:2325-2335.
102. Fraser-Reid B. Some progeny of 2,3-unsaturated sugars-they little resemble grandfather glucose: ten years later. Acc. Chem. Res. 1985, 18:347-354.
103. Koreeda M., Houston T.A., Shull B.K., Klemke E., Tuinman R.J. Iodine-catalyzed Ferrier reaction. 1. A mild and highly versatile glycosylation of hydroxyl and phenolic groups. Synlett 1995, 90-92.
104. Marco J.L. A new and simple synthesis of (+)-threo-ephedrine and (-)-threo-ephedrine. J. Chem. Res. 1988, S2:51.
105. Prasad J.S., Clive D.L.J., Da Silva G.V.J. Synthetic studies related to compactin-use of tri-O-acetyl-d-glucal for preparation of chiral cyclohexenes. J. Org. Chem. 1986, 51:2717-2721.
106. Card P.J. Synthesis of benzannelated pyranosides. J. Org. Chem. 1982, 47:2167-2173.
107. Talekar R.R., Wightman R.H. Synthesis of some pyrrolo[2,3-d]pyrimidine and 1,2,3-triazole isonucleosides. Tetrahedron 1997, 53:3831-3842.
108. Moravcova J., Capkova J., Stanek J. One-pot synthesis of 1,2-O-isopropylideneα-d-xylofuranose. Carbohydr. Res. 1994, 263:61-66.
109. Defaye J., Horton D., Muesser M. Methanolysis of 1,2-O-isopropylidene-5-O-p-tolylsulfonyl-pentofuranoses-influence of steric factors on the formation of 2,5-anhydropentose dimethyl acetals. Carbohydr. Res. 1971, 20:305-318.
110. Cristalli G., Franchetti P., Grifantini M., Vittori S., Lupidi G., Riva F., Bordoni T., Geroni C., Verini M.A. Adenosine-deaminase inhibitors-synthesis and biological-activity of deaza anaolgs of erythro-9-(2-hydroxy-3-nonyl)adenine. J. Med. Chem. 1988, 31:390-393.
111. Yang Z.J., Yu H.W., Min J.M., Ma L.T., Zhang L.H. Stereoselective synthesis of 4-deoxy-4-nucleobase-2,5-anhydro-l-mannitol derivatives. Tetrahedron Asymm. 1997, 8:2739-2747.
112. Yu H.W., Zhang H.Y., Yang Z.J., Min J.M., Ma L.T., Zhang L.H. Studies on the syntheses and biological activities of isonucleosides. Pure Appl. Chem. 1998, 70:435-438.
113. Hong J.H., Lee K., Choi Y., Chu C.K. Enantiomeric synthesis of 3'-fluoro-apionucleosides using Claisen rearrangement. Tetrahedron Lett. 1998, 39:3443-3446.
114. David S., Thieffry A., Veyrieres A. A mild procedures for the regiospecific benzylation and allylation of polyhydroxy-compounds via their stannylene derivatives in non-polar solvents. J. Chem. Soc., Perkin Trans. I 1981, 1796-1801.
115. Lee K., Choi Y., Hong J.H., Schinazi R.F., Chu C.K. New classes of fluorinated l-nucleosides; synthesis and antiviral activity. Nucleosides Nucleotides 1999, 18:537-540.
116. Hong J.H., Gao M.Y., Chu C.K. Synthesis of novel 3'-C-methyl-4'-thio apionucleosides via highly enantioselective elaboration of quaternary carbon by [3,3]-sigmatropic rearrangement. Tetrahedron Lett. 1999, 40:231-234.
117. Hong J.H., Gao M.-Y., Choi Y., Cheng Y.-C., Schinazi R.F., Chu C.K. Synthesis of novel 3'-C-methyl-apionucleosides: an asymmetric construction of a quaternary carbon by Claisen rearrangement. Carbohydr. Res. 2000, 328:37-48.
118. Chu C.K., Beach J.W., Jeong L.S., Choi B.G., Comer F.I., Alves A.J., Schinazi R.F. Enantiomeric synthesis of (+)-BCH-189-[(+)-(2S,5R)-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-cytosine] from d-Mannose and its anti-HIV activity. J. Org. Chem. 1991, 56:6503-6505.
119. Jeong L.S., Alves A.J., Carrigan S.W., Kim H.O., Beach J.W., Chu C.K. An efficient synthesis of enantiomerically pure (+)-(2S,5R)-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-cytosine [(+)-BCH-189] from d-galactose. Tetrahedron Lett. 1992, 33:595-598.
120. Jeong L.S., Schinazi R.F., Beach J.W., Kim H.O., Shanmuganathan K., Nampalli S., Chun M.W., Chung W.K., Choi B.G., Chu C.K. Structure-activity relationships of β-d-(2S,5R)- and α-d-(2S,5S)-1,3-oxathiolanyl nucleosides as potential anti-HIV agents. J. Med. Chem. 1993, 36:2627-2638.
121. Beach J.W., Jeong L.S., Alves A.J., Pohl D., Kim H.O., Chang C.N., Doong S.L., Schinazi R.F., Cheng Y.-C., Chu C.K. Synthesis of enantiomerically pure (2'R,5'S)-(-)-1-[2-(hydroxymethyl)oxathiola n-5-yl]-cytosine as a potent antiviral agent against hepatitis B virus (HBV) and human immunodeficiency virus (HIV). J. Org. Chem. 1992, 57:2217-2219.
122. Jeong L.S., Shinazi R.F., Beach J.W., Kim H.O., Nampalli S., Shanmuganathan K., Alves A.J., McMillan A., Chu C.K., Mathis R. Asymmetric synthesis and biological evaluation of β-l-(2R,5S)- and α-l-(2R,5R)-1,3-oxatholanyl-pyrimidine nucleosides as potential anti-HIV agents. J. Med. Chem. 1993, 36:181-195.
123. Kim H.O., Ahn S.K., Alves A.J., Beach J.W., Jeong L.S., Choi B.G., VanRoey P., Schinazi R.F., Chu C.K. Asymmetric synthesis of 1,3-dioxolane pyrimidine nucleosides and their anti-HIV activity. J. Med. Chem. 1992, 35:1987-1995.
124. Kim H.O., Schinazi R.F., Nampalli S., Shanmuganathan K., Cannon D.L., Alves A.J., Jeong L.S., Beach J.W., Chu C.K. 1,3-Dioxolanylpurine nucleosides (2R,4R) and (2R,4S) with selective anti-HIV activity in human lymphocytes. J. Med. Chem. 1993, 36:30-37.
125. Kim H.O., Shanmuganathan K., Alves A.J., Jeong L.S., Beach J.W., Schinazi R.F., Chang C.N., Cheng Y.-C., Chu C.K. Potent anti-HIV and anti-HBV activities of (-)-lβ-dioxolane-C- and (+)-lβ-dioxolane-T and their asymmetric syntheses. Tetrahedron Lett. 1992, 33:6899-6902.
126. Kim H.O., Schinazi R.F., Shanmuganathan K., Jeong L.S., Beach J.W., Nampalli S., Cannon D., Chu C.K. lβ-(2S,4S)-dioxolanyl and lα-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents-asymmetric synthesis and structure-activity relationships. J. Med. Chem. 1993, 36:519-528.
127. Evans C.A., Dixit D.M., Siddiqui A., Jin H., Allan Tse H.L., Cimpoia A., Bednarski K., Breining T., Mansour T.S. Divergent asymmetric synthesis of dioxolane nucleosides analogs. Tetrahedron Asymm. 1993, 4:2319-2322.
128. Du J., Qu F.C., Lee D.W., Newton M.G., Chu C.K. 1,3-Dioxolane C-nucleosides-asymmetric synthesis of 4 stereoisomers of 2-[2-(hydroxymethyl)-1,3-dioxolan-5-yl]-1,3-thiazole-4-carboxamide. Tetrahedron Lett. 1995, 36:8167-8170.
129. Qu F., Hong J.H., Du J., Newton M.G., Chu C.K. Asymmetric synthesis of (2'R,4'R) and (2'S,4'S)-1,3-dioxolanyl triazole C-nucleosides. Tetrahedron 1999, 55:9073-9088.
130. Shealy Y.F., Clayton J.D. 9-[β-Dl-2α,3α-dihydroxy-4β-(hydroxymethyl)cyclopentyl]adenine, the carbocyclic analog of adenosine. J. Am. Chem. Soc. 1966, 88:3885-3887.
131. Kusaka T., Yamamoto H., Shibata M., Muroi M., Kishi T., Mizuno K. Streptomyces citricolor nov. sp. And a new antibiotic, aristeromycin. J. Antibiot. 1968, 21:255-263.
132. Hayashi M., Yaginuma S., Muto N., Tsujino M. Structures of neplanocins, new antitumor antibiotics. Nucleic Acids Synp. Ser. 1980, 8:S65-S67.
133. De Clerq E. Antiviral and antimetabolic activities of neplanocins. Antimicrob. Agents. chemother. 1985, 28:84-89.
134. Borthwick A.D., Butt S., Biggadike K., Exall A.M., Roberts S.M., Youds P.M., Kirk B.E., Booth B.R., Cameron J.M., Cox S.W., Marr C.L.P., Shill M.D. Synthesis and enzymatic resolution of carbocyclic 2'-ara-fluoro-guanosine - a potent new anti-herpetic agent. J. Chem. Soc., Chem. Commun. 1988, 656-658.
135. Borthwick A.D., Kirk B.E., Biggadike K., Exall A.M., Butt S., Roberts S.M., Knight D.J., Coates J.A.V., Ryan D.M. Fluorocarbocyclic nucleosides - synthesis and antiviral activity of 2'-fluorocarbocyclic and 6'-fluorocarbocyclic 2'-deoxyguanosines. J. Med. Chem. 1991, 34:907-914.
136. De Clercq E. Carbocyclic adenosine analogs as S-adenosylhomocysteine hydrolase inhibitors and antiviral agents: recent advances. Nucleosides Nucleotides. 1998, 17:625-634.
137. Boehme R.E., Storer R., Williamson C., Clemens I.R., Cameron J.M. Abstract of Papers, Interscience Conference on Antimicrobial Agents and Chemotherapy October 1990, Abstract 1088.
138. Bisacchi G.S., Chao S.T., Bachard C., Daris J.P., Innaimo S., Jacobs G.A., Kocy O., Lapointe P., Martel A., Merchant Z., Slusarchyk W.A., Sundeen J.E., Youg M.G., Colonno R., Zahler R. BMS-200475, a novel carbocyclic 2'-deoxyadenosine analog with potent and selective anti-hepatitis B virus activity in vitro. Bioorg. Med. Chem. Lett. 1997, 7:127-132.
139. Katagiri N., Nomura M., Sato H., Kaneko C., Yusa K., Tsuruo T. Synthesis of nucleosides and related compounds -synthesis and anti-HIV activity of 9-[C-4, T-5-bis (hydroxymethyl)cyclopent-2-en-R-1-yl]-9H-adenine. J. Med. Chem. 1992, 35:1882-1886.
140. Vince R., Hua M. Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides. J. Med. Chem. 1990, 33:17-21.
141. Daluge S.M., Good S.S., Faletto M.B., Miller W.H., St Clair M.H., Boone L.R., Tisdale M., Parry N.R., Reardon J.E., Dornsife R.E., Averett D.R., Krenitsky T.A. antimicrob. Agents Chemother. 1592U89, A novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity 1997, 41:1082-1093.
142. Dobkin J.F. Abacavir enters the clinic. Infect. Med. 1999, 16:7.
143. Borthwick A.D., Biggadike K. Synthesis of chiral carbocyclic nucleosides. Tetrahedron. 1992, 48:571-623.
144. Agrofoglio L., Suhas E., Farese A., Condom R., Challand S.R., Earl R.A., Guedj R. Synthesis of carbocyclic nucleosides. Tetrahedron 1994, 50:10611.
145. Agrofoglio L., Suhas E., Farese A., Condom R., Challand S.R., Earl R.A., Guedj R. Synthesis of carbocyclic nucleosides. Tetrahedron 1994, 50:10670.
146. Crimmins M.T. New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron 1998, 54:9229-9272.
147. Marquez V.E., Lim M.-I., Tseng C.K.-H., Markovac A., Priest M.A., Khan M.S., Kaskar B. Total synthesis of (-)-neplanocin A. J. Org. Chem. 1988, 53:5709-5714.
148. Lim M.-I., Marquez V.E. Total synthesis of (-)-neplanocin A. Tetrahedron Lett. 1983, 24:5559-5562.
149. Lim M.-I., Marquez V.E. A synthetic approach towards neplanocin A: preparation of the optically active cyclopentene moiety from d-ribose. Tetrahedron Lett. 1983, 24:4051-4054.
150. Altmann K.-H., Kesselring R., Francotte E., Rihs G. 4',6'-Methano carbocyclic thymidine: a conformationally constrained building block for oligonucleotides. Tetrahedron Lett. 1994, 35:2331-2334.
151. Yoshikawa M., Okaichi Y., Cha B.C., Kitagawa I. Synthesis of (-)-aristeromycin from d-glucose. Tetrahedron 1990, 46:7459-7470.
152. Yoshikawa M., Okaichi Y., Cha B.C., Kitagawa I. Synthesis of (-)-aristeromycin from d-glucose. Chem. Pharm. Bull. 1989, 37:2555-2557.
153. Wolfe M.S., Anderson B.L., Borcherding D.R., Borchardt R.T. Enantiospecific syntheses of aristeromycin and neplanocin A. J. Org. Chem. 1990, 55:4712-4717.
154. Wolfe M.S., Borcherding D.R., Borchardt R.T. A 9-step enantiospecific synthesis of (-)-aristeromycin from d-ribonic acid γ-lactone. Tetrahedron Lett. 1989, 30:1453-1456.
155. Borcherding D.R., Scholtz S.A., Borchardt R.T. Synthesis of analogs of neplanocin A: utilization of optically active dihydroxycyclopentenones derived from carbohydrates. J. Org. Chem. 1987, 52:5457-5461.
156. Bélanger P., Prasit P. Carbocycles from carbohydrates: a simple route to an enantiomerically pure prostaglandin intermediate. Tetrahedron Lett. 1988, 29:5521-5524.
157. Ali S.M., Ramesh K., Borchardt R.T. Efficient enantioselective syntheses of carbocyclic nucleoside and prostaglandin synthons. Tetrahedron Lett. 1990, 31:1509-1512.
158. Wang P., Agrofoglio L., Newton M.G., Chu C.K. Asymmetric synthesis of l-cyclopentyl carbocyclic nucleosides. Tetrahedron Lett. 1997, 38:4207-4210.
159. Wang P., Schinazi R.F., Chu C.K. Asymmetric synthesis and anti-HIV activity of l-carbocyclic 2',3'-didehydro-2',3'-dideoxyadenosine. Bioorg. Med. Chem. Lett. 1998, 8:1585-1588.
160. Wang P., Agrofoglio L.A., Newton M.G., Chu C.K. Chiral synthesis of carbocyclic analogs of l-ribofuranosides. J. Org. Chem. 1999, 64:4173-4178.
161. Wang P., Gullen B., Newton M.G., Cheng Y.-C., Schinazi R.F., Chu C.K. Asymmetric synthesis and antiviral activities of l-carbocyclic 2',3'-didehydro-2',3'-dideoxy and 2',3'-dideoxy nucleosides. J. Med. Chem. 1999, 42:3390-3399.
162. Song G.Y., Paul V., Choo H., Morrey J., Sidwell R.W., Schinazi R.F., Chu C.K. Enantiomeric synthesis of d- and l-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus. J. Med. Chem. 2001, 44:3985-3993.
163. Tadano K.-I., Hoshino M., Ogawa S., Suami T. Transformation of d-erythrose to some pseudo-aldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and 1R,2S,3R,4R-2,3,4-trihydroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine. J. Org. Chem. 1988, 53:1427-1432.
164. Tadano K.-I., Maeda H., Hoshino M., Iimura Y., Suami T. A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose. Synthesis of derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1-(hydroxymethyl)cyclopentane. J. Org. Chem. 1987, 52:1946-1956.
165. Tadano K.-I., Hoshino M., Ogawa S., Suami T. An alternative synthesis of (1R,2S,3R,4R)-2,3-dihydroxy-4-hydroxymethyl-1-cyclopentanamine, a synthetic intermediate of (-)-aristeromycin. Tetrahedron Lett. 1987, 28:2741-2744.
166. Tadano K.-I., Maeda H., Hoshino M., Iimura Y., Suami T. A new transformation of aldose derived synthons to pseudo-hexopyranose or pseudo-pentofuranose derivatives. Chem. Lett. 1986, 1081-1084.
167. Ballou C.E., Fischer H.O.L., MacDonald D.L. The synthesis and properties of d-erythrose 4-phosphate. J. Am. Chem. Soc. 1955, 77:5967-5970.
168. Vanhessche K., González Bello C., Vandewalle Total synthesis of (-)-neplanocin A from l-ribulose. Synlett. 1991, 921-922.
169. Vanhessche K., Van der Eycken E., Vandewalle M. l-Ribulose: a novel chiral pool compound. Tetrahedron Lett. 1990, 31:2337-2340.
170. Park K.H., Rapoport H. Enantioselective synthesis of (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene, a precursor for carbocyclic nucleoside synthesis. J. Org. Chem. 1994, 59:394-399.
171. Gerspacher M., Rapoport H. 2-Amino-2-deoxyhexoses as chiral educts for hydroxylated indolizidines. Synthesis of (+)-castanospermine and (+)-epicastanospermine. J. Org. Chem. 1991, 56:3700-3706.
172. Yoshikawa M., Yokokawa Y., Inoue Y., Yamaguchi S., Murakami N. Facile syntheses of pseudoα-d-arabinofuranose, and two pseudo-d-arabinofuranosylnucleosides, (+)-cyclaradine and (+)-1-pseudoβ-d-arabinofuranosyluracil, from d-arabinose. Tetrahedron 1994, 50:9961-9974.
173. Ohira S., Sawamoto T., Yamato M. Synthesis of (-)-neplanocin A via C-H insertion of alkylidenecarbene. Tetrahedron Lett. 1995, 36:1537-1538.
174. Chong Y., Gumina G., Chu C.K. A divergent synthesis of d- and l-carbocyclic 4'-fluoro-2',3'-dideoxynucleosides as potential antiviral agents. Tetrahedron Asymm. 2000, 11:4853-4875.
175. 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.
176. Lee M.G., Du J.F., Chun M.W., Chu C.K. Enantiomeric synthesis of l-(or 1'R, 2'S)-carbocyclic cyclopropyl nucleosides. J. Org. Chem. 1997, 62:1991-1995.
177. Zhao Y., Yang T.-F., Lee M.G., Lee D.-W., Newton M.G., Chu C.K. Asymmetric synthesis of (1'S,2'R)-cyclopropyl carbocyclic nucleosides. J. Org. Chem. 1995, 60:5236-5242.
178. Lee M.G., Lee D., Zhao Y., Newton M.G., Chu C.K. Enantioselective synthesis of cyclopropyl carbocyclic l-nucleosides. Tetrahedron Lett. 1995, 36:3499-3502.
179. Yang T.-F., Kim H., Kotra L.P., Chu C.K. Design and synthesis of 2'-hydroxyethylcyclopropyl carbocyclic nucleosides. Tetrahedron Lett. 1996, 37:8849-8852.
180. Zhao Y.F., Lee M.G., Yang T.-F., Chun B.K., Du J.F., Schinazi R.F., Chu C.K. Asymmetric synthesis of cyclopropyl carbocyclic nucleosides. Nucleosides Nucleotides 1995, 14:303-305.
181. Zhao Y., Yang T.-F., Lee M.G., Chun B.K., Du J., Schinazi R.F., Lee D.-W., Newton M.G., Chu C.K. Synthesis of enantiomerically pure cyclopropyl carbocyclic nucleosides. Tetrahedron Lett. 1994, 35:5405-5408.
182. Pierra C., Olgen S., Cavalcanti S.C.H., Cheng Y.-C., Schinazi R.F., Chu C.K. Synthesis and antiviral activities of enantiomeric 1-[2-(hydroxymethyl)-cyclopropyl]methyl nucleosides. Nucleosides Nucleotides 2000, 19:253-268.
183. Xiang Y., Du J., Chu C.K. Syntheses of 2',3'-dideoxy-d-C-nucleosides from γ-lactone. Nucleosides Nucleotides 1996, 15:1821-1834.
184. Beach J.W., Kim H.O., Jeong L.S., Nampalli S., Islam Q., Ahn S.K., Babu J.R., Chu C.K. A highly stereoselective synthesis of anti-HIV 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides. J. Org. Chem. 1992, 57:3887-3894.
185. Liang C., Ma T., Cooperwood J.S., Du J., Chu C.K. Synthesis of l-ribofuranosyl C-nucleosides. Carbohydrate Research 1997, 303:33-38.
186. Ma T., Pai S.B., Zhu Y.L., Lin J.S., Shanmuganathan K., Du J., Wang C., Kim H., Newton M.G., Cheng Y.-C., Chu C.K. Structure-activity relationships of 1-(2-deoxy-2-fluoroβ-l-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents. J. Med. Chem. 1996, 39:2835-2843.
187. Tam S.Y.-K., Klein R.S., Wempen I., Fox J.J. Nucleosides. 112. Synthesis of some new pyrazolol[1,5-a]-1,3,5-triazines and their C-nucleosides. J. Org. Chem. 1979, 44:4547-4553.
188. Tam S.Y.-K., Hwang J.S., De Las Heras F.G., Klein R.S., Fox J.J. Nucleosides. 105. Synthesis of 8-(β-d-ribofuranosyl)pyrazolo [1,5-a]-1,3,5-triazine isosteres of adenosine and inosine. J. Heterocycl. Chem. 1976, 13:1305-1308.
189. Lim M.-I., Klein R.S. Synthesis of 9-deazaadenosine - a new cytotoxic C-nucleoside isostere of adenosine. Tetrahedron Lett. 1981, 22:25-28.
190. Hammerschmidt F., Peric B., Öhler E. Synthesis of d-apioβ-d-furanosyl maleimide, an analog of showdomycin with transposed hydroxymethyl group. Monatsh. Chem. 1997, 128:183-190.
191. Drescher M., Hammerschmidt F. A second synthesis of d-apioβ-d-furanosyl maleimide as a structural analog of showdomycin. Monatsh. Chem. 1997, 128:713-723.
192. Kozikowski A.P., Ames A. Total synthesis of the C-nucleoside Dl-showdomycin by a Diels-Alder, retrograde Dieckmann strategy. J. Am. Chem. Soc. 1981, 103:3923-3924.
193. Chun B.K., Chu C.K. Asymmetric synthesis of carbocyclic C-nucleoside, (-)-9-deazaaristeromycin. Tetrahedron Lett. 1999, 40:3309-3312.
194. Chu C.K., Ma T., Shanmuganathan K., Wang C., Xiang Y., Pai S.B., Yao G.-Q., Sommadossi J.-P., Cheng Y.-C. Use of 2'-fluoro-5-methylβ-l-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Empstein-Barr Virus. Antimicrob. Agents Chemother. 1995, 39:979-981.
195. Chu C.K., Hong J.H., Choi Y., Du J., Lee K., Chun B.K., Boudinot F.D., Peek S.F., Korba B.E., Tennant B.C., Cheng Y.-C.L-FMAU Drugs of the Future. 1998, 23:821-826.
196. Xiang Y., Kotra L.P., Chu C.K., Schinazi R.F. Synthesis and anti-HIV activities of 2'-deoxy-2',2″-difluoroβ-l-ribofuranosyl-pyrimidine and-purine nucleosides. Bioorg. Med. Chem. Lett. 1995, 5:743-748.
197. Kotra L.P., Xiang Y., Newton M.G., Schinazi R.F., Cheng Y.-C., Chu C.K. Structure-activity relationships of 2'-deoxy-2',2'-difluoro-l-erythro-pentofuranosyl nucleosides. J. Med. Chem. 1997, 40:3635-3644.
198. Kotra L.P., Newton M.G., Chu C.K. Synthesis of 2,3-dideoxy-2,2-difluoro-l-glycero-pentofuranosyl nucleosides. Carbohydr. Res. 1998, 306:69-80.
199. Xiang Y., Cavalcanti S., Chu C.K., Schinazi R.F., Pai S.B., Zhu Y.-L., Cheng Y.-C. Anti-human immunodeficiency virus type-1 (HIV-1) and anti-hepatitis B virus (HBV) activities of (2,3-dideoxy-2-fluoroβ-l-threo- pentofuranosyl)nucleosides. Bioorg. Med. Chem. Lett. 1995, 5:877-880.
200. Ma T., Lin J.-S., Newton M.G., Cheng Y.-C., Chu C.K. Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoroβ-l-arabinofuranosyl)purine nucleosides. J. Med. Chem. 1997, 40:2750-2754.
201. Choi Y., Lee K., Hong J.H., Schinazi R.F., Chu C.K. Synthesis and anti-HIV activity of l-2'-fluoro-2',3'-unsaturated purine nucleosides. Tetrahedron Lett. 1998, 39:4437-4440.
202. Lee K., Choi Y., Gullen E., Schlueter-Wirts S., Schinazi R.F., Cheng Y.-C., Chu C.K. Synthesis and anti-HIV and anti-HBV activities of 2'-fluoro-2',3'-unsaturated l-nucleosides. J. Med. Chem. 1999, 42:1320-1328.
203. Pai S.B., Liotta D.C., Chu C.K., Schinazi R.F. Inhibition of hepatitis B virus by novel 2'-fluoro-2',3'-unsaturated d- and l-nucleosides. 3rd International Conference on Therapies for Viral Hepatitis, Maui, USA 1999, Abstract 125, International Society for Antiviral Therapy.
204. Lee K., Choi Y., Schinazi R.F., Chu C.K. Structure-activity relationships of 2'-fluoro-2',3'-unsaturated d-nucleosides as anti-HIV-1 agents. 218th American Chemical Society National Meeting 1999, August 22-26.
205. Lee K., Choi Y., Gumina G., Zhou W., Schinazi R.F., Chu C.K. Structure-activity relationships of 2'-fluoro-2',3'-unsaturated d-nucleosides as anti-HIV agents. J. Med. Chem. 2002, 45:1313-1320.
206. Gumina G., Schinazi R.F., Chu C.K. Synthesis and potent anti-HIV activity of l-3'-fluoro unsaturated citidine. Org. Lett. 2001, 3:4177-4180.
207. Gumina G., Zhou W., Schinazi R.F., Chu C.K. Synthesis of l-3'-fluoro unsaturated nucleosides as potential antiviral agents. 222nd American Chemical Society National Meeting 2001, August 26-30.
208. Zhou W., Gumina G., Schinazi R.F., Chu C.K. Synthesis of 3'-fluoro-2',3'-unsaturated D-nucleosides. 222nd American Chemical Society National Meeting 2001, August 26-30.
209. El Ashry E.S.H., El Kilany Y. Acyclonucleosides: Part 1. Seco-nucleosides. Adv. Heterocycl. Chem. 1997, 67:391-438.
210. El Ashry E.S.H., El Kilany Y. Acyclonucleosides: Part 2. Diseco-nucleosides. Adv. Heterocycl. Chem. 1997, 68:1-88.
211. El Ashry E.S.H., El Kilany Y. Acyclonucleosides: Part 3. Tri-tetra-, and pentaseco-nucleosides. Adv. Heterocycl. Chem. 1998, 69:129-215.
212. Chu C.K., Cutler S. Chemistry and antiviral activities of acyclonucleosides. J. Heterocyclic Chem. 1986, 23:289-319.
213. Okumura K., Oine T., Yamada Y., Tomie M., Adachi T., Nagura T., Kawazu M., Mizoguchi T., Inoue I. Synthetic studies on eritadenine. I. Reactions of some purines with the 2,3-O-protected dihydroxybutyrolactone. J. Org. Chem. 1971, 36:1573-1579.
214. Barker R., MacDonald D.L. Some oxidation and reduction products of 2,4-O-ethylidene-d-erythrose. J. Am. Chem. Soc. 1960, 82:2301-2303.
215. Baker D.C., Hawkins L.D. Synthesis of inhibitors of adenosine deaminase. A total synthesis of erythro-3-(adenin-9-yl)-2-nonanol and its isomers from chiral precursors. J. Org. Chem. 1982, 47:2179-2184.
216. Bukhari M.A., Foster A.B., Lehmann J., Webber J.M. Aspects of stereochemistry. Part X. Isopropylidene derivatives of l-rhamnitol. J. Chem. Soc. 1963, 2287-2890.
217. Richtmyer N.K., Hudson C.S. A direct proof of the equivalence of carbon atoms 1 and 6 in d-mannitol and a new method of correlating certain higher-carbon sugars and alcohols. J. Am. Chem. Soc. 1950, 72:3880-3884.
218. MacCoss M., Chen A., Tolman R.L. Syntheses of all four possible diastereomers of the acyclonucleoside 9-(1,3,4-trihydroxy-2-butoxymethyl)guanine from carbohydrate precursors. Tetrahedron Lett. 1985, 26:4287-4290.
219. Dondoni A., Fogagnolo M., Medici A., Pedrini P. Diastereoselectivity in the 1,2-addition of silylazoles to chiral aldehydes. Stereocontrolled homologation of α-hydroxyaldehydes. Tetrahedron Lett. 1985, 26:5477-5480.
220. Ashton W.T., Canning L.F., Reynolds G.F., Tolman R.L., Karkas J.D., Liou R., Davies M.-E.M., DeWitt C.M., Perry H.C., Field A.K. Synthesis and antiherpetic activity of (S)-, (R)-, and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'- deoxyguanosine. J. Med. Chem. 1985, 28:926-933.
221. Ullas G.V., Chu C.K., Ahn M.K., Kosugi Y. Synthesis of C-nucleoside analog of (S)-9-(2,3-dihydroxypropyl) adenine and related acyclonucleosides. J. Org. Chem. 1998, 53:2413-2418.
222. Buchanan J.G., Craven D.A., Wightman R.H., Harnden M.R. C-Nucleoside studies. Part 21. Synthesis of some hydroxylalkylated pyrrolo- and thieno-[3,2-d]pyrimidines related to known antiviral acyclonucleosides. J. Chem. Soc. Perkin Trans. 1 1991, 195-202.
223. Lin T.-S., Mu S.-P., Liu M.-C., Mancini W.R. Synthesis of (R)-and (S)-1-([2-hydroxy-1-(aminome thyl)ethoxy]methyl)-5-benzyluracil, potent inhibitors of uridine phosphorylase. Nucleosides Nucleotides 1990, 9:559-568.
224. Howe R.J., Malkin T.J. An X-ray and thermal examination of the glycerides. Part XI. The 1:2-diglycerides, and futher observations on 1:3-diglycerides. J. Chem. Soc. 1951, 2663-2667.
225. Herdewijn P., Van Aerschot A., Busson R., Claes P., De Clerq E. Synthesis of 2'-deoxy-2'-fluoro-d-arabinopyranosyl nucleosides and their 3',4'-seco analogs. Nucleosides Nucleotides 1991, 10:1525-1549.
226. Shimada N., Hasegawa S., Harada T., Tomisawa T., Fujii A., Takita T. Oxetanocin, a novel nucleoside from bacteria. J. Antibiotics 1986, 39:1623-1625.
227. Hoshino H., Shimizu N., Shimada N., Takita T., Takeuchi T. Inhibition of infectivity of human immunodeficiency virus by oxetanocin. J. Antibiotics 1987, 40:1077-1078.
228. Ichikawa E., Kato K. Synthesis of oxetanocin A and related unusual nucleosides with bis(hydroxymethyl)-branched sugars. Synthesis 2002, 1-28.
229. Wilson F.X., Fleet G.W.J., Vogt K., Wang Y., Witty D.R., Choi S., Storer R., Myers P.L., Wallis C.J. Synthesis of oxetanocin. Tetrahedron Lett. 1990, 31:6931-6934.
230. Saksena A.K., Ganguly A.K., Girihavallabhan V.M., Pike R.E., Chen Y.-T., Puar M.S. Ring contraction reactions of 2-O-methanesulfonates of α-hydroxyγ-lactones in aqueous medium to oxetane-2-carboxylic acids: a convenient synthesis of 3'-O-methyloxetanocin and a formal synthesis of oxetanocin. Tetrahedron Lett. 1992, 33:7721-7724.
231. Gumina G., Chu C.K. Total synthesis of l-oxetanocin. Abstr. Papers Am. Chem. Soc. 2002, CARB 002.
232. Gumina G., Chu C.K. Synthesis of l-Oxetanocin. Org. Lett. 2002, 4:1147-1149.
233. Chu C.K., Beach J.W., Babu J.R., Jeong L.S., Jeong H.K., Ahn S.K., Islam Q., Lee S.J., Chen Y. Stereoselective synthesis of 2',3'-dideoxy and 2',3'-didehydro-2',3'-dideoxy-nucleosides. Nucleosides Nucleotides 1991, 10:423-426.
234. Beach J.W., Kim H.O., Jeong L.S., Nampalli S., Islam Q., Ahn S.K., Babu J.R., Chu C.K. A highly stereoselective synthesis of anti-HIV 2',3'-dideoxy- and 2',3'-didehydro-2',3'-dideoxynucleosides. J. Org. Chem. 1992, 57:3887-3894.
235. Jeong L.S., Beach J.W., Chu C.K. Stereoselective synthesis of 3-azido-2,3-dideoxy-d-ribose derivatives and its utilization for the synthesis of anti-HIV nucleosides. J. Heterocycl. Chem. 1993, 30:1445-1452.
236. Yang T.-F., Kotra L.P., Teng Q., Naguib F.N.M., Sommadossi J.-P., El Kouni M., Chu C.K. Tetrahedron Lett. 1995, 36:983-986.
237. Giri I., Bolon P.J., Chu C.K. Synthesis of 2'-Cα-methyl-2',3'-dideoxynucleosides. Nucleosides Nucleotides 1996, 15:183-204.
238. Nair V., Emanuel D.J. Synthetic design, stereochemistry, and enzymatic activity of a reversed aminoacyl nucleoside: an analog of puromycin. J. Am. Chem. Soc. 1977, 99:1571-1576.
239. Pickering L., Nair V. Novel bicyclic nucleoside analogs related to natural griseolic acids. Nucleosides Nucleotides 1997, 16:1435-1438.
240. Chao Q., Zhang J., Pickering L., Jahnke T.S., Nair V. Concise and stereospecific synthesis of novel bicyclic dideoxynucleosides as potential antiviral agents. Tetrahedron 1998, 54:3113-3124.