Approach to carbocyclic 4-deoxypyrazofurin through asymmetrisation of a meso-norbornene derivative

Synlett

Volumn , Issue 12, 1997, Pages 1467-1468

  Mohar, Barbara ^a   Kobe, Jože ^a   Koomen, Gerrit Jan ^b  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006652858     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1044     Document Type: Article

References (30)

1. (a) Marquez V.E.; Lim M.-I. Med. Res. Rev. 1986, 6, 1.
2. (b) Borthwick, A.D.; Biggadike, K. Tetrahedron 1992, 48, 571.
3. (c) Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.R.; Earl, R.A.; Guedj, R. Tetrahedron 1994, 50, 10611.
4. nd vol., pp. 89.
5. Sauer, D.R.; Schneller, S.W. Synthesis 1991, 747.
6. Mohar, B.; Štimac, A.; Kobe, J. Tetrahedron: Asymmetry 1994, 5, 863.
7. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1969, 91, 3075.
8. Syntheses of (-)-aristeromycin: (a) Arita, M.; Adachi, K.; Ito, Y.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1983, 105, 4049.
9. (b) Arai, Y.; Hayashi, Y.; Yamamoto, M.; Takayema, H.; Koizumi, T. J. Chem. Soc. Perkin Trans. I 1988, 3133.
10. (c) Takayama, H.; Iyobe, A.; Koizumi, T. J. Chem. Soc., Chem. Commun. 1986, 771.
11. (d) Katagiri, N.; Haneda, T.; Watanabe, N.; Hayasaka, E.; Kaneko, C. Chem. Pharm. Bull. 1988, 36, 3867.
12. (e) Helmchen, G.; Krotz, A.; Neumann, H.P.; Ziegler, M. Liebigs Ann. Chem. 1993, 1313. Syntheses of carbarifto C-nucleosides:
13. (f) Mohar, B.; Štimac, A.; Kobe, J. Nucleosides & Nucleotides 1993,1 2, 793.
14. (g) Mohar, B.; Kobe, J. Nucleosides & Nucleotides 1997, 16, in press.
15. (a) Brown, H.C.; Desai, M.C.; Jadhav, P.K. J. Org. Chem. 1982, 47, 5065.
16. (b) Brown, H.C.; Joshi, N.N. J. Org. Chem. 1988, 53, 4059.
17. Jadhav, P.K.; Brown, H.C. J. Org. Chem. 1981, 46, 2988.
18. (a) Burgess, K.; Ohlmeyer, M.J. J. Org. Chem.. 1988, 53, 5179.
19. (b) Sato, M.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1990, 31, 231.
20. (a) Uozumi, Y.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 9887.
21. (b) Uozumi, Y.; Hayashi, T. Tetrahedron Lett. 1993, 34, 2335.
22. (c) Hayashi, T. Acta Chem. Scandinavica 1996, 50, 259.
23. (d) Synthesis of (S)-MOP: Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
24. 2O and the combined filtrates concentrated. The residue was boiled with pentane for 20 min, filtered, and concentrated to give ketone 4 (7.34 g, 67%). An analytical sample was purified by flash chromatography using petrolether/EtOAc (5:1) as eluent.
25. 2O (4 x 30 mL) to obtain alcohol 3 and 3-pinanol that were oxidised with PDC as described in ref. 10. The resulted mixture was carefully fractionated to remove 3-pinanone (bp 55°C/0.2 Torr) from ketone 4.
26. 2BH. Ketone 4 was separated from by-product with column chromatography using petrolether/ EtOAc (8:1) as eluent.
27. 4). Concentration gave crude 3 that was oxidised with PDC as described in ref. 10 to furnish ketone 4.
28. Recently, a synthesis of O-benzyl protected acetamide 8 was published: Boyer, S.; Leahy, J. J. Org. Chem. 1997, 62, 3976.
29. Brown, H.; Heim, P. J. Org. Chem. 1973, 38, 912.
30. 4 242.115. Found 242.115.