Synthesis of novel cyclopropyl carbocyclic nucleosides from (-)-(Z)-2,3-methanohomoserine

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1221-1223

  Rifé, Joan ^a   Ortuño, Rosa M ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000772937     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990203w     Document Type: Article

References (22)

1. Kusaka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1968, 21, 255. Yaginuma, S.; Tsujino, M.; Muto, N.; Otani, M.; Hatashi, M.; Ishimura, F.; Fujii, T.; Watanabe, S.; Matsuda, T.; Watanabe, T.; Abe, J. Curr. Chemother. Infect. Dis., Int. Congr. 1980, 2, 1558.
2. Kusaka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1968, 21, 255. Yaginuma, S.; Tsujino, M.; Muto, N.; Otani, M.; Hatashi, M.; Ishimura, F.; Fujii, T.; Watanabe, S.; Matsuda, T.; Watanabe, T.; Abe, J. Curr. Chemother. Infect. Dis., Int. Congr. 1980, 2, 1558.
3. Yaginuma, S.; Tsujino, M.; Muto, N.; Otani, M.; Hatashi, M.; Ishimura, F.; Fujii, T.; Watanabe, S.; Matsuda, T.; Watanabe, T.; Abe, J. Curr. Chemother. Infect. Dis., Int. Congr. 1980, 2, 1558.
4. Maag, H.; Nelson, J. T.; Steiner, J. L. R.; Prisbe, E. J. J. Med. Chem. 1994, 37, 431.
5. Sekiyama, T.; Hatsuya, S.; Tanaka, Y.; Uchiyama, M.; Ono, N.; Iwayama, S.; Oikawa, M.; Suzuki, K.; Okunishi, M.; Tsuji, T. J. Med. Chem. 1998, 41, 1284.
6. (a) Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441.
7. (b) Csuk, R.; Kern, A. Tetrahedron 1999, 55, 8409.
8. Yang, T.-F.; Kim, H.; Kotra, L. P.; Chu, C. K. Tetrahedron Lett. 1996, 49, 8849.
9. Harnden, M. R.; Jarvest, R. L.; Bacon, T. H.; Boyd, M. R. J. Med. Chem. 1987, 30, 1636.
10. (a) Csuk, R.; Eversmann, L. Tetrahedron 1998, 54, 6445.
11. (b) Csuk, R.; Thiede, G. Tetrahedron 1999, 55, 739.
12. (a) Gauvry, N.; Huet, F. Tetrahedron 1999, 55, 1321.
13. (b) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236.
14. (b) Lee, G.; Du, J. F.; Chun, M. W.; Chu, C. K. J. Org. Chem. 1997, 62, 1991.
15. Jiménez, J. M.; Rifé, J.; Ortuño, R. M. Tetrahedron: Asymmetry 1999, 7, 537.
16. (a) Shaw, G.; Warrener, R. N. J. Chem. Soc. 1958, 153.
17. (b) Shealy, Y. F.; O'Dell, C. A.; Thorpe, M. C. J. Heterocycl. Chem. 1981, 18, 383.
18. (c) Díaz, M.; Ortuño, R. M. Tetrahedron: Asymmetry 1997, 8, 3421.
19. All new products were fully charaterized by their physical constants and spectroscopic data and gave satisfactory microanalysis.
20. 2-methanol as eluent) to afford compound 9 (149 mg, 47% yield).
21. max260, ∈ 15000), thus discarding the presence of the N-3 regioisomer.
22. See. for instance: Jung, M. E.; Kiankarimi, M. J. Org. Chem. 1998, 63, 8133.