Expedient approach to chiral cyclobutanones: Asymmetric synthesis of cyclobut-G

Organic Letters

Volumn 10, Issue 5, 2008, Pages 821-824

  Darses, Benjamin ^a   Greene, Andrew E ^a   Coote, Susannah C ^a   Poisson, Jean François ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; DRUG DERIVATIVE; GUANINE; LOBUCAVIR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOBUTANES; GUANINE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 43549090706     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702977x     Document Type: Article

References (48)

1. (a) Wiberg, K. B. In The Chemistry of Cyclobutanes; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons, Ltd.: West Sussex, England, 2005; Vol. 1, Chapter 1.
2. (b) Lee-Ruff, E.; Mladenova, G. Chem. Rev. 2003, 103, 1449-1483.
3. (a) Fu, N.-Y.; Chan, S.-H.; Wong, H. N. C. In The Chemistry of Cyclobutanes; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons, Ltd.: West Sussex, England, 2005; Vol. 1, Chapter 9.
4. (b) Namyslo, J. C; Kaufmann, D. E. Chem. Rev. 2003, 103, 1485-1538.
5. (c) Bellus, D.; Ernst, B. Angew. Chem., Int. Ed. Engl. 1988, 27, 797- 827.
6. (a) Hansen, T. V.; Stenstrom, Y. Naturally Occurring Cyclobutanes. In Organic Synthesis Theory and Applications; Hudlicky, T., Ed.; Elsevier Science Ltd.: New York, 2001; Vol. 5, pp 1-38.
7. (b) Taber, D. F.; Frankowski, K. J. J. Org. Chem. 2005, 70, 6417-6421 and references therein.
8. Lee-Ruff, E. In The Chemistry of Cyclobutanes; Rappoport, Z.; Liebman, J. F., Eds.; John Wiley & Sons, Ltd.: West Sussex, England, 2005; Vol. 1, Chapter 8.
9. For recent approaches limited to bicyclic adducts, see:
10. (a) Canales, E.; Corey, E. J. J. Am. Chem. Soc. 2007, 729, 12686-12687.
11. (b) Luzung, M. R.; Mauleon, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 729, 12402-12403. See also:
12. (c) Honda, T.; Kimura, N. J. Chem. Soc. Chem. Commun. 1994, 77-78.
13. (d) Hazelard, D.; Fadel, A. Tetrahedron: Asymmetry 2005, 16, 2067-2070.
14. Cyclopentanones: (a) Greene, A. E.; Charbonnier, F.; Luche, M.-J.; Moyano, A. J. Am. Chem. Soc. 1987, 709, 4752-4753.
15. (b) Kanazawa, A.; Delair, P.; Pourashraf, M.; Greene, A. E. J. Chem. Soc. Perkin Trans. 1 1997, 1911-1912.
16. Lactones: (a) B. M. de Azevedo, M.; Murta, M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567-4569.
17. (b) Murta, M. M.; De Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1993, 58, 7537-7541.
18. (c) De Azevedo, M. B. M.; Greene, A. E. J. Org. Chem. 1995, 60, 4940-4942.
19. Pyrrolidinones: (a) Ncbois, P.; Greene, A. E. J. Org. Chem. 1996, 67, 5210-5211.
20. (b) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660-4663.
21. (c) Delair, P.; Brot. E.; Kanazawa. A.; Greene, A. E, J. Org. Chem. 1999, 64, 1383-1386.
22. (d) Pourashraf, M.; Delair, P.; Rasmussen. M. O.; Greene, A. E. J. Org. Chem. 2000, 65, 6966-6972.
23. (e) Rasmussen, M. O.; Delair, P.; Greene. A. E. J. Org. Chem. 2001, 66, 5438-5443.
24. (f) Roche, C; Delair, P.; Greene. A. E. Org. Lett. 2003. 5, 1741-1744.
25. (g) Muniz, M. N.; Kanazawa, A.; Greene, A. E. Synleti 2005, 1328-1330.
26. (h) Ceccon, J.; Poisson. J. F.; Greene, A. E. Synlett 2005, 1413-1416.
27. (i) Roche, C; Kadlecikova, K.; Veyron, A.; Delair. P.; Philouze, C; Greene, A. E.; Fiot, D.; Burghammer, M. J. Org. Chem. 2005, 70, 8352-8363.
28. (j) Ceccon, I; Greene, A. E.; Poisson. J. F. Org. Lett. 2006, 8, 4739-4742.
29. For selected references, see: (a) Jeffs, P. W.; Molina. G.; Cass, M. W.; Cortege, N. A. J. Org. Chem. 1982, 47, 3871-3875.
30. (b) Johnston, B.D.; Slessor, K. N.; Oehlschlager, A. C. J. Org. Chem. 1985, 50, 114-117.
31. (c) Redlich, H.; Lenfers, J. B.; Kopf. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 777-778.
32. (d) Hanna, I.; Pan, J.; Lallemand, J.-Y. Synlett 1991, 511-512.
33. (e) Paquette, L. A.; Heidelbaugh, T. M. Synthesis 1998, 495-508.
34. Kami, N.; Bernardes, V.; Greene, A. E. Org. Synth. 1997, 74, 13-22.
35. Delair. P.; Kanazawa. A. M.; de Azevedo, M. B. M.; Greene, A. E. Tetrahedron: Asymmetry 1996, 7, 2707 2710. (R)- and (S)-Sterico1 [l-(2,4.6-triisopropylphenyl)ethanol] are now commercially available from Sigma-Aldrich.
36. The cis-eno! ethers were prepared from Stericol (52-71% yields) by the procedure described in ref 10.
37. 2o (10 ml.) at 20 °C was added Zn-Cu (480 mg, 7.3 mmol), followed by trichloroacetyl chloride (0.11 ml, 1.0 mmol) dropwise over 30 min. A saturated solution of ammonium chloride in methanol (20 ml) was then added, and the resulting mixture was refluxed for 10 min. The crude product was isolated in the usual way and purified by flash chromatography on silica gel to afford cyclobutanone 3.
38. Except for the cycloadditions of the benzyl- and allyl-substituted enol ethers lb and 1c. these cycloadditions have not been previously reported.
39. (a) Malherbe, R.; Bellus, D. Helv. Chim. Acta 1978, 61, 3096-3099.
40. (b) For a minireview. see: Gonda. J. Angew. Chem., Int. Ed. 2004, 43, 3516-3524.
41. (a) Bisacchi, G. S.; Braitman. A.; Cianci. C. W.; Clark, J. M.; Field, A. K.; Hagen. M. E.; Hockstein, D. R.; Malley. M. F.; Mitt, T.; Slusarchyk. W. A.; Sundeen, J. E.; Terry, B. J.; Tuomari, A. V.; Weaver, E. R.; Young, M. G.; Zaliler. R. J, Med. Chem. 1991, 34, 1415-1421.
42. (b) Bisacchi, G. S.; Singh, J.; Godfrey, J. D., Jr.; Kissick, T. P.; Mitt, T.; Malley, M. F.; Di Marco, J. D.; Gougoutas. J. Z.; Mueller. R. H.; Zahler, R. J. Org. Chem.1995, 60, 2902-2905.
43. (c) Singh, J.; Bisacchi, G. S.; Ahmad, S.; Godfrey, J. D., Jr.; Kissick, T. P.; Mitt, T.; Kocy, O.; Vu. T.; Papaioannou, C. G.; Wong, M. K.; Heikes. J. E.; Zahler, R.; Mueller, R. H. Org. Process Res. Dev. 1998, 2, 393-399.
44. (d) Genovesi, E. V.; Lamb, L.; Medina, I.; Taylor, D.; Seifer, M.; Innaimo, S.; Colonno, R. J.; Clark, J. M. Antiviral Res. 2000, 48, 197 203.
45. (e) Hanson, R. L.; Shi, Z.; Brzozowski, D. B.; Banerjee, A.; Kissick. T. P.; Singh, J.; Pullockaran, A. J.; North, J. T.; Fan, J.; Howell, J.; Durand, S. C; Montana. M. A.; Kronenthal, D. R.; Mueller, R. H.; Patel, R. N. Bioorg. Med. Chem. 2000, 8, 2681-2687.
46. (a) Hoshino, FL; Shimizu, N.; Shimada, N.; Takita, T.; Takeuehi. T. J. Antibiot. 1987, 40, 1077-1078. For additional references to this and related compounds, see:
47. (b) Rustullet, A.; Alibés, R.; de March, P.; Figueredo, M.; Font, J. Org. Lett. 2007, 9, 2827-2830.
48. R (enantiomer) = 18.0 min.