The first synthesis of a 2',3'-methano carbocyclic nucleoside

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 9069-9072

  Katagiri, Nobuya ^a   Yamatoya, Yoshitsugu ^a   Ishikura, Minoru ^a  

^a HEALTH SCIENCES UNIVERSITY OF HOKKAIDO   (Japan)

Author keywords

2',3' methano carbocyclic nucleoside; 2 Azabicyclo 2.2.1 hept 5 en 3 one; Diazomethane; Photolysis

Indexed keywords

CARBOCYCLIC NUCLEOSIDE; DIAZOMETHANE; NUCLEOSIDE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; PARTIAL DRUG SYNTHESIS; PHOTOLYSIS; STRUCTURE ANALYSIS;

EID: 0033579637     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01910-3     Document Type: Article

References (23)

1. Part ILV of Synthesis of nucleosides and their related compounds. For Part ILIV, see: Katagiri, N.; Morishita, Y; Oosawa, U.; Yamaguchi, M. Tetrahedron Lett. 1999, 40, 6835-6840.
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9. Katagiri, N.; Takebayashi, M.; Kokufuda, H.; Kaneko, C.; Kanehira, K.; Torihara, M. J. Org. Chem. 1997, 62, 1580-1581.
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11. Unpublished results.
12. An etheral solution of diazomethane containing methanol was obtained from the treatment of N-methyl-N-nitroso-p- toluenesulfonylamide with sodium hydroxide in methanol-water whereas methanol free diazomethane-ether solution was prepared using carbitol instead of methanol.
13. 3): 1.48 (9H, s), 1.92 (2H, m), 2.31 (1H, dd, J=6.3, 2.7 Hz), 2.83 (1H, m), 3.72 (3H, s), 4.39 (1H, dd, J=18.3, 8.4 Hz), 4.44 (1H, br s), 4.66 (1H, d, J=18.4 Hz), 4.93 (1H, br s), 5.41 (1H, br s).
14. Katagiri, N.; Matsuhashi, Y; Kokufuda, H.; Takebayashi, M.; Kaneko, C. Tetrahedron Lett. 1997, 38, 1645-1648. The exo-selectivity would be due to pyramidarization [Williams, R. V.; Gadgil, V. R.; Garner, G. G.; Williams, J. D.; Vij, S. Tetrahedron Lett. 1999, 40, 2689-2690, and references cited therein] or Cieplak effect [Cieplack, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447-8462] as observed in the selectivity for the addition to a double bond of bicyclic compound.
15. Katagiri, N.; Matsuhashi, Y; Kokufuda, H.; Takebayashi, M.; Kaneko, C. Tetrahedron Lett. 1997, 38, 1645-1648. The exo-selectivity would be due to pyramidarization [Williams, R. V.; Gadgil, V. R.; Garner, G. G.; Williams, J. D.; Vij, S. Tetrahedron Lett. 1999, 40, 2689-2690, and references cited therein] or Cieplak effect [Cieplack, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447-8462] as observed in the selectivity for the addition to a double bond of bicyclic compound.
16. Katagiri, N.; Matsuhashi, Y; Kokufuda, H.; Takebayashi, M.; Kaneko, C. Tetrahedron Lett. 1997, 38, 1645-1648. The exo-selectivity would be due to pyramidarization [Williams, R. V.; Gadgil, V. R.; Garner, G. G.; Williams, J. D.; Vij, S. Tetrahedron Lett. 1999, 40, 2689-2690, and references cited therein] or Cieplak effect [Cieplack, A. S.; Tait, B. D.; Johnson, C. R. J. Am. Chem. Soc. 1989, 111, 8447-8462] as observed in the selectivity for the addition to a double bond of bicyclic compound.
17. Compound 4 was prepared in 54% yield by refluxing of 1 in methanol with catalytic amount of conc. hydrochloric acid for 4 h, mp 36°C.
18. 3): 0.83 (1H, br d, J=11.4 Hz), 1.53 (9H, s), 1.86 (1H, br d, J=11.4 Hz), 2.54-2.65 (1H, m), 3.47 (1H, br s), 4.23 (1H, dt, J=19.0, 4.2 Hz), 4.29 (1H, br s), 4.59 (1H, ddd, J=19.0, 9.8, 1.5 Hz), 5.28 (1H, br dd, J=7.1, 1.1 Hz).
19. 3): 0.00 (1H, m, overlapped with TMS), 0.49 (1H, dt, J=8.3, 5.4 Hz), 1.34 (2H, m), 1.44 (10H, s and m), 1.78 (1H, dt, J=14.6, 7.3 Hz), 2.16 (1H, dt, J=8.8, 4.4 Hz), 2.80 (1H, br), 3.58 (1H, dd, J=10.3, 4.4 Hz), 3.70 (1H, dd, J=10.3, 3.9 Hz), 4.00 (1H, br), 5.90 (1H, d, NH).
20. Katagiri, N.; Muto, M.; Kaneko, C. Tetrahedron Lett. 1989, 30, 1645-1648.
21. 5O: C, 59.25; H, 5.39; N, 28.79. Found: C, 59.15; H, 5.50; N, 28.63.
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