Conformationally locked carbocyclic nucleosides: Synthesis of the 1-methyl-6-oxabicyclo[3.1.0]hexane scaffold

Synlett

Volumn , Issue 14, 2006, Pages 2215-2218

  Aubin, Yoann ^a   Audran, Gérard ^a   Monti, Honoré ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Carbocyclic nucleosides; Conformationally locked nucleosides; Lipase regioselectivity; Mitsunobu reaction; Stereoselective synthesis

Indexed keywords

1 METHYL 6 OXABICYCLO[3.1.0]HEXANE; CARBOCYCLIC NUCLEOSIDE; HEXANE; NUCLEIC ACID BASE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DEACETYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ISOMERIZATION; MITSUNOBU REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; STEREOCHEMISTRY;

EID: 33748711218     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949635     Document Type: Article

References (59)

1. (a) Marquez, V. E. In Advances in Antiviral Drug Design, Vol 2; De Clercq, E., Ed.; JAI Press Inc.: Greenwich, CT, 1996, 89-146.
2. (b) Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998.
3. (c) Recent Advances in Nucleosides: Chemistry and Chemotherapy; Chu, C. K., Ed.; Elsevier Science: Amsterdam, 2002.
4. (a) Agrofolio, L. A.; Challaud, S. R. Acyclic, Carbocyclic and l-Nucleosides; Kluwer Academic Publishers: Dordrecht, Boston, London, 1998. Recent reviews:
5. (b) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
6. (c) Ferrero, M.; Gotor, V. Chem. Rev. 2000, 100, 4319.
7. (d) Rodriguez, J. B.; Comin, M. J. Mini-Rev. Med. Chem. 2003, 3, 95.
8. (a) Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550.
9. (b) Marquez, V. E.; Lim, M. Med. Res. Rev. 1986, 6, 1.
10. (c) Roberts, S.; Biggadike, K.; Borthwick, A. D.; Kirk, B. In Topics in Medicinal Chemistry; Leeming, P. R., Ed.; Royal Society of Chemistry: London, 1988.
11. (d) Saunders, J.; Cameron, J. M. Med. Res. Rev. 1995, 15, 497.
12. For selected recent syntheses and references cited therein, see: (a) Caamaño, O.; Gomez, G.; Fernández, F.; Garcia, M. D.; Garcia-Mera, X.; De Clercq, E. Synthesis 2004, 2855.
13. (b) Takagi, C.; Sukeda, M.; Kim, H.-S.; Wataya, Y.; Yabe, S.; Kitade, Y.; Matsuda, A.; Shuto, S. Org. Biomol. Chem. 2005, 3, 1245.
14. (c) Yang, M.; Schneller, S. W. Bioorg. Med. Chem. 2005, 13, 877.
15. (d) Santaniello, E.; Ciuffreda, P.; Alessandrini, L. Synthesis 2005, 509.
16. (e) Cho, J. H.; Bernard, D. L.; Sidwell, R. W.; Kern, E. R.; Chu, C. K. J. Med. Chem. 2006, 49, 1140.
17. (f) Yang, M.; Zhou, J.; Schneller, S. W. Tetrahedron 2006, 62, 1295.
18. (g) Agrofoglio, L. A. Curr. Org. Chem. 2006, 10, 333.
19. For selected recent syntheses and references cited therein, see: (a) Moon, H. R.; Lee, H. J.; Kim, K. R.; Lee, K. M.; Lee, S. K.; Kim, H. O.; Chun, M. W.; Jeong, L. S. Bioorg. Med. Chem. 2004, 14, 5641.
20. (b) Kim, J. W.; Choi, B. G.; Hong, J. H. Bull. Korean Chem. Soc. 2004, 25, 1812.
21. (c) Zhu, X.-F.; Nydegger, F.; Gossauer, A. Helv. Chim. Acta 2004, 87, 2245.
22. (d) Gonzalez-Moa, M. J.; Besada, P.; Teijeira, M.; Teran, C.; Uriate, E. Synthesis 2004, 543.
23. (e) Quadrelli, P.; Scrocchi, R.; Caramella, P.; Rescifina, A.; Piperno, A. Tetrahedron 2004, 60, 3643.
24. (f) Yang, Y.-Y.; Meng, W.-D.; Qing, F.-L. Org. Lett. 2004, 6, 4257.
25. (g) Hegedus, L. S.; Cross, J. J. Org. Chem. 2004, 69, 8492.
26. (h) Wang, J.; Jin, Y.; Rapp, K. L.; Bennett, M.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2005, 48, 3736.
27. (i) Meillon, J.-C.; Griffe, L.; Storer, R.; Gosselin, G. Nucleosides, Nucleotides Nucleic Acids 2005, 24, 695.
28. (j) García, M. D.; Caamaño, G.; Fernández, F.; Lopez, C.; De Clercq, E. Synthesis 2005, 925.
29. (k) Lee, J. A.; Moon, H. R.; Kim, H. O.; Kim, K. R.; Lee, K. M.; Kim, B. T.; Hwang, K. J.; Chun, M. W.; Jacobson, K. A.; Jeong, L. S. J. Org. Chem. 2005, 70, 5006.
30. (l) Roy, A.; Schneller, S. W.; Keith, K. A.; Hartline, C. B.; Kern, E. R. Bioorg. Med. Chem. 2005, 13, 4443.
31. (m) Jin, Y. L.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1366.
32. (n) Oh, C. H.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1520.
33. (o) Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2005, 26, 1767.
34. (p) Jiang, M. X.-W.; Jin, B.; Gage, J. L.; Priour, A.; Savela, G.; Miller, M. J. J. Org. Chem. 2006, 71, 4164.
35. (q) Ludek, O. R.; Krämer, T.; Balzarini, J.; Meier, C. Synthesis 2006, 1313.
36. (r) García, M. D.; Caamaño, O.; Fernández, F.; Abeijon, P.; Blanco, J. M. Synthesis 2006, 73.
37. (s) Gosselin, G.; Griffe, L.; Meillon, J.-C.; Storer, R. Tetrahedron 2006, 62, 906.
38. For selected recent syntheses and references cited therein, see: (a) Ishikura, M.; Matsumoto, K.; Hasunuma, M.; Katagiri, N. Heterocycles 2003, 60, 2737.
39. (b) Choi, Y.; George, C.; Comin, M. J.; Barchi, J. J. Jr.; Kim, H. S.; Jacobson, K. A.; Balzarini, J.; Mitsuya, H.; Boyer, P. L.; Hughes, S. H.; Marquez, V. E. J. Med. Chem. 2003, 46, 3292.
40. (c) Choi, Y.; Moon, H. R.; Yoshimura, Y.; Marquez, V. E. Nucleosides, Nucleotides Nucleic Acids 2003, 22, 547.
41. (d) Comin, M. J.; Rodriguez, J. B.; Russ, P.; Marquez, V. E. Tetrahedron 2003, 59, 295.
42. (e) Kim, K. W.; Hong, J. H. Bull. Korean Chem. Soc. 2004, 25, 668.
43. (f) Ishikura, M.; Matsumoto, K.; Murakami, A. Heterocycles 2004, 64, 241.
44. (g) Paoli, L.; Piccini, S.; Rodriguez, M.; Sega, A. J. Org. Chem. 2004, 69, 2881.
45. (h) Moon, H. R.; Kim, K. R.; Kim, B. T.; Hwang, K. J.; Chun, M. W.; Jeong, L. S. Nucleosides, Nucleotides Nucleic Acids 2005, 24, 709.
46. (i) Tchilibon, S.; Joshi, B. V.; Kim, S.-K.; Duong, H. T.; Gao, Z.-G.; Jacobson, K. A. J. Med. Chem. 2005, 48, 1745.
47. (j) Joschi, B. V.; Moon, H. R.; Fettinger, J. C.; Marquez, V. E.; Jacobson, K. A. J. Org. Chem. 2005, 70, 439.
48. (k) Comin, M. J.; Parrish, D. A.; Deschamps, J. R.; Marquez, V. E. Org. Lett. 2006, 8, 705.
49. Audran, G.; Acherar, S.; Monti, H. Eur. J. Org. Chem. 2003, 92.
50. Nucleoside numbering.
51. (a) Mitsunobu, O. Synthesis 1981, 1.
52. (b) Jenny, T. F.; Horlacher, J.; Previsani, N.; Benner, S. A. Helv. Chim. Acta 1992, 75, 1944.
53. (c) Review: Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127.
54. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons, Inc.: New York, 1999, 150.
55. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
56. (a) Sharpless, K. B.; Michaelson, R. C. J. Org. Chem. 1973, 38, 6136.
57. (b) Sharpless, K. B.; Teranichi, A. Y.; Backväll, J.-E. J. Am. Chem. Soc. 1977, 99, 3120.
58. 3 (950 mg, 3.6 mmol, 1.5 equiv) in fresly distilled THF (50 mL) kept under Ar atmosphere at 0 °C. The mixture was stirred for 30 min and then the purine base was added (3.6 mmol, 1.5 equiv). The mixture was stirred for an additional 30 min and then a solution of epoxide 7 (450 mg, 2.4 mmol, 1 equiv) in dry THF (5 mL) was added slowly. The cooling bath was removed and the mixture allowed to warm to r.t. The mixture was stirred for 12 h at r.t.(chloropurine) or 12 h at r.t. then 4 h at 40 °C (adenine, 2-aminochloropurine). The solvent was removed under reduced pressure and the residue was chromatographed on a silica gel column (gradients hexane-EtOAc as eluent). Compounds 8 (66% yield) and 9 (56% yield) were obtained pure as white solids, but 10 was contaminated with inseparable triphenylphosphine oxide.
59. 2 before aminocyclopropanation. Using this protocol, pure 12 was obtained in 53% overall yield from 7.