Chiral synthons for CARBA-β-D-ribonucleosides. Synthesis of CARBA-4- deoxypyrazofurin and isomeric CARBA-4-deaza-oxoformycin analogues

Nucleosides and Nucleotides

Volumn 18, Issue 3, 1999, Pages 443-456

  Mohar, Barbara ^a   Kobe, Jože ^a  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

(4 HYDROXYMETHYL 2,3 ISOPROPYLIDENEDIOXY 1 CYCLOPENTYL) METHYL BUTYRATE; 4 DEAZA OXOFORMYCIN; 4 DEOXYPIRAZOFURIN; 6,7 (ISOPROPYLIDENEDIOXY) 3 OXABICYCLO[3.2.1]OCTANE 2 ONE; CYCLOALKANE DERIVATIVE; RIBONUCLEOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0032896401     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257779908043088     Document Type: Article

References (23)

1. Moser, H.E; Hurley, H.H.; Sun, D.; Fox, K.R. Drugs Acting on Nucleic Acids and Nucleic Acid Processing Enzymes. In Perspectives in Medicinal Chemistry; Testa, B.; Kyburz, E.; Fuhrer, W.; Giger, R., Eds.; VHCA: Basel, 1993; pp. 275-297.
2. Mohar, B.; Štimac, A.; Kobe, J. Nucleosides & Nucleotides 1993, 12, 793.
3. Mohar, B.; Štimac, A.; Kobe, J. Tetrahedron: Asymmetry 1994, 5, 863.
4. Mohar, B.; Kobe, J. Nucleosides & Nucleotides 1997, 16, 1427.
5. Mohar, B.; Koomen, G.-J.; Kobe, J. Synlett, 1997, 1467.
6. (a) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049.
7. (b) Arai, Y.; Hayashi, Y.; Yamamoto, M.; Takayema, H.; Koizumi, T. J. Chem. Soc. Perkin Trans. I 1988, 3133.
8. (c) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771.
9. (d) Katagiri, N.; Haneda, T.; Watanabe, N.; Hayasaka, E.; Kaneko, C. Chem. Pharm. Bull. 1988, 36, 3867.
10. Sauer, D.R.; Schneller, S.W. Synthesis 1991, 747.
11. Prhavc, M.; Kobe, J. Nucleosides & Nucleotides 1996, 15, 1779.
12. Corey, E.J.; Suggs, J. Tetrahedron Lett. 1975, 2647.
13. Synthesis of racemic nitrile 9a: Just, G.; Reader, G. Tetrahedron Lett. 1973, 17, 1525.
14. Fernández, R.; Gasch, C.; Lassaletta, J.-M.; Llera, J.-M. Vázquez, J. Tetrahedron Lett. 1993, 34, 141.
15. Synthesis of O-benzyl protected acetamide 10: Boyer, S.; Leahy, J. J. Org. Chem. 1997, 62, 3976.
16. Carotti, A.; Campagna, F.; Ballini, R. Synthesis, 1979, 56.
17. Brown, H.; Heim, P. J. Org. Chem. 1973, 38, 912.
18. Acton, E.M.; Ryan, K.J. In Nucleic Acid Chemistry, Improved and New Synthetic Procedures, Methods, and Techniques; Townsend, L.B.; Tipson, R.S., Eds.; Wiley: New York, 1978; Part 1, pp. 475-480.
19. Roeder, G. Chem. Ber. 1913, 46, 2563.
20. Hargreaves, M.K.; Pritchard, J.G.; Dave, H.R. Chem. Rev. 1970, 70, 439.
21. Polak, M.; Mohar, B.; Kobe, J.; Plavec J. J. Am. Chem. Soc. 1998, 120, 2508.
22. Hofman-Bang, N. Acta Chem. Scand. 1957, 11, 581.
23. Bryson, T.A.; Dolak, T.M. Org. Synth. Coll. vol. 6., 505.