An expeditious route to carbocyclic nucleosides: (-)-Aristeromycin and (-)-carbodine

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 3, 1997, Pages 247-250

  Burlina, Fabienne ^a   Favre, Alain ^b   Fourrey, Jean Louis ^a   Thomas, Martial ^a  

^a CNRS   (France)

^b INSTITUT JACQUES MONOD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARISTEROMYCIN; CARBOCYCLIC NUCLEOSIDE; CARBODINE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031552104     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00619-1     Document Type: Article

References (33)

1. 1) For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. For biosynthesis see: Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev. 1995, 169-176. For recent synthetic efforts see: Zhang, D.; Gosh, A.; Süling, C; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799-3802. Trost, B. M.; Madsen, R.; Guile, S. G.; Elia, E. H. E. Angew. Chem Int. Ed. Engl. 1996, 35, 1569-1571.
2. 1) For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. For biosynthesis see: Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev. 1995, 169-176. For recent synthetic efforts see: Zhang, D.; Gosh, A.; Süling, C; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799-3802. Trost, B. M.; Madsen, R.; Guile, S. G.; Elia, E. H. E. Angew. Chem Int. Ed. Engl. 1996, 35, 1569-1571.
3. 1) For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. For biosynthesis see: Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev. 1995, 169-176. For recent synthetic efforts see: Zhang, D.; Gosh, A.; Süling, C; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799-3802. Trost, B. M.; Madsen, R.; Guile, S. G.; Elia, E. H. E. Angew. Chem Int. Ed. Engl. 1996, 35, 1569-1571.
4. 1) For a recent review see: Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670. For biosynthesis see: Jenkins, G. N.; Turner, N. J. Chem. Soc. Rev. 1995, 169-176. For recent synthetic efforts see: Zhang, D.; Gosh, A.; Süling, C; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799-3802. Trost, B. M.; Madsen, R.; Guile, S. G.; Elia, E. H. E. Angew. Chem Int. Ed. Engl. 1996, 35, 1569-1571.
5. 2) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1-40. Montgomery, J. A. Acc. Chem. Res. 1986, 19, 293-300. Hobbs, J. B. Comprehensive Medicinal Chemistry; Hansch, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: Oxford, 1990; Vol. 2, pp 306-322.
6. 2) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1-40. Montgomery, J. A. Acc. Chem. Res. 1986, 19, 293-300. Hobbs, J. B. Comprehensive Medicinal Chemistry; Hansch, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: Oxford, 1990; Vol. 2, pp 306-322.
7. 2) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1-40. Montgomery, J. A. Acc. Chem. Res. 1986, 19, 293-300. Hobbs, J. B. Comprehensive Medicinal Chemistry; Hansch, C.; Sammes, P. G.; Taylor, J. B., Eds.; Pergamon: Oxford, 1990; Vol. 2, pp 306-322.
8. 3) Kishi, T; Muroi, M.; Kusaka, T.; Nishikawa, M.; Kamiya, K.; Mizuno, K. Chem. Pharm. Bull. 1972, 20, 940-946.
9. 4) Wolfe, M. S.; Borchardt, R. T. J. Med. Chem. 1991, 34, 1521-1530.
10. 5) Moser, H. E. Perspectives Med. Chem., Testa, B.; Kyburz, E.; Fuhrer, W.; Giger, R., Eds.; Verlag Helvetica Chemica Acta, Basel, 1993; pp. 275-297. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194. De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374. For the incorporation of (-)-aristeromycin in a fully 2',5'-trinucleotide see: Sawai, H.; Lesiak, K.; Imai, J.; Torrence, P. F. J. Med Chem. 1985, 28, 1376-1380.
11. 5) Moser, H. E. Perspectives Med. Chem., Testa, B.; Kyburz, E.; Fuhrer, W.; Giger, R., Eds.; Verlag Helvetica Chemica Acta, Basel, 1993; pp. 275-297. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194. De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374. For the incorporation of (-)-aristeromycin in a fully 2',5'-trinucleotide see: Sawai, H.; Lesiak, K.; Imai, J.; Torrence, P. F. J. Med Chem. 1985, 28, 1376-1380.
12. 5) Moser, H. E. Perspectives Med. Chem., Testa, B.; Kyburz, E.; Fuhrer, W.; Giger, R., Eds.; Verlag Helvetica Chemica Acta, Basel, 1993; pp. 275-297. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194. De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374. For the incorporation of (-)-aristeromycin in a fully 2',5'-trinucleotide see: Sawai, H.; Lesiak, K.; Imai, J.; Torrence, P. F. J. Med Chem. 1985, 28, 1376-1380.
13. 5) Moser, H. E. Perspectives Med. Chem., Testa, B.; Kyburz, E.; Fuhrer, W.; Giger, R., Eds.; Verlag Helvetica Chemica Acta, Basel, 1993; pp. 275-297. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123-6194. De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374. For the incorporation of (-)-aristeromycin in a fully 2',5'-trinucleotide see: Sawai, H.; Lesiak, K.; Imai, J.; Torrence, P. F. J. Med Chem. 1985, 28, 1376-1380.
14. 6) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311.
15. 7) Burlina, F.; Clivio, P.; Fourrey, J.-L.; Riche, C.; Thomas, M. Tetrahedron Lett. 1994, 35, 8151-8152.
16. 10b
17. 9) (a) Saville-Stones, E. A.; Lindell, S. D.; Jennings, N. S.; Head, J. C.; Ford, M. J. J. Chem. Soc., Perkins Trans. I, 1991, 2603-2604.
18. (b) Roberts, S. M.; Shoberu, K. A. J. Chem. Soc., Perkins Trans. I, 1991, 2605-2607.
19. 10) (a) Popescu, A.; Hörnfeldt, A.-B.; Gronowitz, S. Nucleosides Nucleotides 1995, 14, 1233-1249.
20. (b) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkins Trans. I, 1993, 1543-1544.
21. 11) Russ, P. L.; Hegedus, L.; Kelley, J. A.; Barchi Jr, J. J.; Marquez, V. E. Nucleosides Nucleotides 1992, 11, 351-363.
22. 12) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622. Trost, B. M.; Li, L.; Guile, S. G. J. Am. Chem. Soc. 1992, 114 , 8745-8747. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
23. 12) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622. Trost, B. M.; Li, L.; Guile, S. G. J. Am. Chem. Soc. 1992, 114 , 8745-8747. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
24. 12) Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622. Trost, B. M.; Li, L.; Guile, S. G. J. Am. Chem. Soc. 1992, 114 , 8745-8747. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
25. 13) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276. See also: Granberg, K. L.; Bäckvall, J.-E. J. Am. Chem Soc. 1992, 114, 6858-6863.
26. 13) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276. See also: Granberg, K. L.; Bäckvall, J.-E. J. Am. Chem Soc. 1992, 114, 6858-6863.
27. Ac; R= Ac) at the expense of diacetate (-)-2. Surprisingly, in a related recent example cytosine was found to give no reaction (Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chemistry Lett. 1994, 1071-1074).
28. 15) It is interesting to note that the stereochemical and regiochemical outcome of the Pd induced reaction involving an allyl acetate, such as derived from cis-4-hydroxymethylenecyclopent-1-en-3-ol, migtht be very dependent of the base (purine or pyrimidine) which is used (see, for instance: Gundersen, L-L.; Benneche, T.; Undheim, K. Tetrahedron Lett. 1992, 33, 1085-1088 and for a discussion: Hodgson, D. H.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans I 1994, 3373-3378).
29. 15) It is interesting to note that the stereochemical and regiochemical outcome of the Pd induced reaction involving an allyl acetate, such as derived from cis-4-hydroxymethylenecyclopent-1-en-3-ol, migtht be very dependent of the base (purine or pyrimidine) which is used (see, for instance: Gundersen, L-L.; Benneche, T.; Undheim, K. Tetrahedron Lett. 1992, 33, 1085-1088 and for a discussion: Hodgson, D. H.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans I 1994, 3373-3378).
30. 16) Da Silva, A. D.; Coimbra, E. S.; Fourrey, J-L.; Machado, A. S.; Robert-Gero, M. Tetrahedron Lett. 1993, 34, 6745-6748.
31. 17) A solution of this problem can now be envisioned after a recent observation by McCague et al. pointing at the strong anti directing effect of a carboxamide function in the dihydroxylation of a cyclopentene system (Palmer, C. F.; McCague, R.; Ruecroft, G.; Savage, S; Taylor, S.J.C; Ries, C. Tetrahedron Lett. 1996, 37, 4601-4604).
32. 2/Methanol system).
33. 19) Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. J. Chem. Soc., Chem. Commun. 1996, 1623-1624.