A convenient synthesis of acyclic adenosines with an unsaturated side chain by modification of 9-(2,3-isopropylidene-d-ribityl)adenine

Nucleosides and Nucleotides

Volumn 17, Issue 8, 1998, Pages 1333-1345

  Hirota, Kosaku ^a   Monguchi, Yasunari ^a   Sajiki, Hironao ^a   Yatome, Chizuko ^b   Hiraoka, Akio ^b   Kitade, Yukio ^b  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE DERIVATIVE; NEPLANOCIN A;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; METHODOLOGY; REACTION ANALYSIS;

EID: 0031823741     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319808003472     Document Type: Article

References (26)

1. (a) De Clercq, E. Biochem. Pharmacol. 1987, 36, 2567-2575.
2. (b) Wolfe, M. S.; Borchardt, R. T. J. Med. Chem. 1991, 34, 1521-1530.
3. (c) Yuan, C. S.; Liu, S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. In Advances in Antiviral Drug Design; DeClercq, E., Ed.; JAI Press Inc.: Greenwich, 1996; Vol. 2, pp. 41-88.
4. (a) Votruba, I.; Holy, A. Collect. Czech. Chem. Commun. 1982, 47, 167-172.
5. (b) Holy, A.; Votruba, I.; De Clercq, E. ibid. 1982, 47, 1392-1407.
6. (c) Merta, A.; Votruba, I.; Vesely, J.; Holy, A. ibid. 1983, 48, 2701-2708.
7. (a) Borchardt, R. T.; Keller, B. T.; Patel-Thombre, U. J. Biol. Chem. 1984, 259, 4353-4358.
8. (b) De Clercq, E. Antimicrob. Agents Chemother. 1985, 28, 84-89.
9. (a) Kitade, Y.; Hirota, K.; Maki, Y. Tetrahedron Lett. 1993, 34, 4835-4836.
10. (b) Hirota, K.; Monguchi, Y.; Kitade, Y.; Sajiki, H. Tetrahedron 1997, 53, 16683-16698.
11. (a) Kitade, Y.; Monguchi, Y.; Hirota, K.; Maki, Y. Tetrahedron Lett. 1993, 34, 6579-6580.
12. (b) Hirota, K.; Monguchi, Y.; Sajiki, H.; Kitade, Y. Synlett, 1997, 697-698.
13. Recentry, Matsuda et al. have utilized the 9-ribityladenine 2 for the synthesis of neplanocin A: Niizuma, S.; Shuto, S.; Matsuda, A. Tetrahedron 1997, 53, 13621-13632.
14. L-Eritadenine exhibits the most inhibitory activity next to D-eritadenine among the four possible stereoisomers toward AdoHcy hydrolase: see, ref. 2a
15. (a) Borcherding, D. R.; Scholtz, S. A.; Borchardt, R. T. J. Org. Chem. 1987, 52, 5457-5461.
16. (b) Hasobe, M.; Mckee, J. G.; Borcherding, D. R.; Borchardt, R. T. Antimicrob. Agents Chemother. 1987, 31, 1849-1851.
17. (c) Narayanan, S. R.; Keller, B. T.; Borcherding, D. R.; Scholtz, S. A.; Borchardt, R. T. J. Med. Chem. 1988, 31, 500-503.
18. (a) Hümmer, W.; Gracza, T.; Jäger, V. Tetrahedron Lett. 1989, 30, 1517-1520.
19. (b) Jäger, V.; Hümmer, W.; Stahl, U.; Gracza, T. Synthesis, 1991, 769-776.
20. Lee et al. have reported that the easy epimerization of 2,3-erythro-aldose acetonide to 2,3-threo-aldose acetonide was observed under the basic conditions: (a) Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, III, L. A.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264. (b) Lee, A. W. M. Magnetic Resonance in Chemistry 1985, 23, 468-469.
21. Lee et al. have reported that the easy epimerization of 2,3-erythro-aldose acetonide to 2,3-threo-aldose acetonide was observed under the basic conditions: (a) Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, III, L. A.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245-264. (b) Lee, A. W. M. Magnetic Resonance in Chemistry 1985, 23, 468-469.
22. 1H NMR spectrum.
23. Lerner, L. M. J. Org. Chem. 1972, 37, 470-473.
24. (a) Palmer, J. L.; Abeles, R. H. J. Biol. Chem. 1976, 257, 5817-5819.
25. (b) Palmer, J. L.; Abeles, R. H. ibid. 1979, 254, 1217-1226.
26. 2Et and subsequent dilute HCl gave the α,β-unsaturated lactone via (Z)-α,β-unsaturated ester. However, we could not purify the lactone D corresponding to Chu's lactone: Chu, C. K.; Beach, J. W.; Ullas, G. V.; Kosugi, Y. Tetrahedron Lett. 1988, 29, 5349-5352.