A highly efficient synthesis of the antiviral agent (+)-cyclaradine involving the regioselective cleavage of epoxide by neighboring participation

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1961-1964

  Katagiri, Nobuya ^a   Matsuhashi, Yumiko ^a   Kokufuda, Hideaki ^a   Takebayashi, Masahiro ^a   Kaneko, Chikara ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CYCLARADINE;

AMINATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0031575786     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00234-7     Document Type: Article

References (26)

1. 1. Part ILI of "Synthesis of nucleosides and their related compounds". For Part IL, see: Katagiri, N.; Makino, M.; Tamura, T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 850.
2. 2. For recent reviews of the synthesis of carbocyclic nucleosides, see: (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
3. (b) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
4. 3. (a) Chien, L. T.; Schabel, Jr., F. M.; Alford, Jr., C. A. in "Selective Inhibitors of Viral Functions", Carter, W. A. Ed., CRC Press, Cleveland, Ohio, 1975, pp 227-256.
5. (b) Pavan-Langston, D.; Buchanan, R. A.; Alford, Jr., C. A. Ed., "Adenine Arabinoside: An Antiviral Agent", Raven Press, New York, N.Y., 1975.
6. (c) Pursoff, W. H.; Ward, D. C. Biochem, Pharmacol 1976, 25, 1223.
7. 4. (a) Lepage, G. A.; Junfa, I. G. Cancer Res. 1965, 25, 46.
8. (b) Koshiura, R.; LePage, G. A. Cancer Res. 1968, 28, 1014.
9. 5. (a) Vince, R.; Daluge, S. J. Med. Chem. 1977, 20, 612.
10. (b) Vince, R.; Daluge, S.; Lee, H.; Shannon, W. M.; Arnett, G.; Schafer, T. W.; Nagabusham, T. L.; Reichert, P.; Tsai, H. Science 1983, 221, 1405.
11. 6. (a) Yoshikawa, M.; Nakae, T.; Cha, B. C.; Yokokawa, Y.; Kitagawa, I. Chem. Pharm. Bull. 1989, 37, 545.
12. (b) Tadano, K.; Kimura, H.; Ogawa, S. Bull Chem. Soc. Jpn. 1989, 62, 1355.
13. (c) Helmchen, G.; Krotz, A.; Neumann, H.-P.; Ziegler, M. L. Liebigs Ann. Chem. 1993, 1313.
14. 7. (a) Yagt, J.; VanLeusen, A. J. Org. Chem. 1974, 39, 564.
15. (b) Daluge, S.; Vince, R. J. Org. Chem. 1978, 43, 2311.
16. 8. Katagiri, N.; Muto, M.; Kaneko, C. Tetrahedron Lett. 1989, 30, 1645.
17. 3O), 3.12 (1H, m, 4-H), 3.62 (1H, dd, J=4.0, 1.5 Hz, 5-or 6-H), 3.75 (1H, dd, J=4.0, 1.5 Hz, 5-or 6-H), 4.97 (1H, m, 1-H).
18. 3).
19. 20-568°±15).
20. 12. Taylor, S. J. C.; Sutherland, A. G.; Lee, C.; Wisdom, R.; Thomas, S.; Roberts, S. M.; Evans, C. J. Chem. Soc. Chem. Commun. 1990, 1120.
21. 3 ).
22. 3).
23. 15. Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C. Tetrahedron Lett. 1994, 35, 5665.
24. 20 +48° (c=1.5, MeOH)).
25. D19 + 62° (c=1.0, CHC13).
26. 18. Recently, (±)-deoxyaraaristeromycin has been synthesized via the inversion of the hydroxy substituent by neighboring participation of the benzoylamino group on the cyclopentane moiety. Frick, W.; Sharadbala, D. P.; Gambino, A. J.; Schneller, S. W. Tetrahedron Lett. 1993, 34, 5541.