Asymmetric synthesis of carbocyclic C-nucleoside, (-)-9- deazaaristeromycin

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3309-3312

  Chun, Byoung K ^a   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Carbocyclic C nucleoside

Indexed keywords

9 DEAZAARISTEROMYCIN; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033597242     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00482-7     Document Type: Article

References (28)

1. 1. (a) Shealy, Y. F.; Clayton, J. D. J. Am. Chem. Soc. 1966, 88, 3885;
2. (b) Kusaka, T.; Yamamoto, H.; Shibata, M.; Murai, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1968, 21, 255;
3. (c) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049;
4. (d) Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17;
5. (e) as recent reviews: Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
6. (e) as recent reviews: Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48,571. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611.
7. 2. (a) Davis, F. F.; Allen, F. W. J. Biol. Chem 1957, 227, 907;
8. (b) Hori, M.; Ito, E.; Takita, T.; Koyama, G.; Tacheuchi, T.; Umezaya, H. J. Antibiot. 1964,17A, 96;
9. (c) Chu, C. K.; Wempen, I.; Watanabe, K. A.; Fox, J. J. J. Org. Chem. 1976, 41, 2793;
10. (d) Liang, C.; Ma, T.; Cooperwood, J. S.; Du, J.; Chu, C. K. Carbohydr. Res. 1997, 303, 33;
11. (e) Lee, C. S.; Du, J.; Chu, C. K. Nucleosides & Nucleotides 1996, 15, 1223;
12. (f). Lim, M.; Klein, R. S. Tetrahedron Lett. 1981, 22, 25;
13. (g) as recent reviews: Watanabe, K. A. In Chemistry of Nucleosides and Nucleotides 1994, vol 3; Townsend, L. B., Ed., Plenum, New York, Chapter 5. Shaban, M. A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1997, 68, 223.
14. (g) as recent reviews:Watanabe, K. A. In Chemistry of Nucleosides and Nucleotides 1994, vol 3; Townsend, L. B., Ed.,Plenum, New York, Chapter 5. Shaban, M. A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1997, 68, 223.
15. 3. (a) Just, G.; Kim, S. Tetrahedron Lett. 1976, 1046;
16. (b) Saksena, A. K.; McPhail, A. T.; Onan, K. D. Tetrahedron Lett. 1981, 22, 2067;
17. (c) Katagiri, N.; Tomura, M.; Haneda, T.; Kaneko, C. J. Chem. Soc. Chem. Commun. 1987, 1422;
18. (d) Hildbrand, S.; Leuman, C.; Scheffold, R. Helv. Chim. Acta. 1996, 79, 702.
19. 4. (a) Takahashi, T.; Kotsubo, H.; Koizumi, T. Tetrahedron: Asymmetry 1991, 2, 1035;
20. (b) Dishington, A. P.; Humber, D. C.; Stoodley, R. J. J. Chem. Soc. Perkin Trans. 1 1993, 57.
21. 5. (a) Wang, P.; Agrofoglio, L. A.; Newton, M. G.; Chu, C. K. Tetrahedron Lett. 1997, 38, 4207;
22. (b) Wolfe, M. S.; Borcherding, D. R.; Borchardt, R. T. Tetrahedron Lett. 1989, 30, 1453;
23. (c) Ali, S. M.; Ramesh, K.; Borchardt, R. T. Tetrahedron Lett. 1990, 31, 1509.
24. 5: C, 63.69; H, 8.61; N, 4.13. Found: C, 63.75; H, 8.52; N, 3.95.
25. 7. Pereyre, M.; Quintard, J.-P.; Rahm, A., Ed. In Tin in Organic Synthesis 1987, Butterworths, London, Chapter 7 and references therein.
26. 8. Xie, M.; Berges, D. A.; Robins, M. J. J. Org. Chem. 1996, 61, 5178.
27. 9. Huber, R.; Vasella, A. Tetrahedron 1990, 46, 33.
28. 3 0.3 MeOH: C, 53.94; H, 6.33; N, 20.46. Found: C, 53.67; H, 6.12; N, 20.11.