Stereoselective synthesis of optically active dihydrofurans and dihydropyrans via a ring closing metathesis reaction

Tetrahedron Asymmetry

Volumn 22, Issue 11, 2011, Pages 1161-1168

  Çayir, Merve ^a   Demirci, Sema ^a   Sezer, Serdar ^a   Tanyeli, Cihangir ^a  

^a MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL ALCOHOL; FURAN DERIVATIVE; HOMOALLYL ALCOHOL; HOMOPROPARGYL ALCOHOL; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DIELS ALDER REACTION; ENANTIOMER; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 80052557317     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.07.003     Document Type: Article

References (58)

1. For reviews, see: (a) Hocek, M.; Stambasky, J.; Kocovsky, P. Chem. Rev. 2009, 109, 6729;
2. Taylor, R. J. K.; McAllister, G. D.; Franck, R. W. Carbohydr. Res. 2006, 341, 1298;
3. Hultin, P. G. Curr. Top. Med. Chem. 2005, 5, 1299;
4. Bililign, T.; Griffith, B. R.; Thorson, J. S. Nat. Prod. Rep. 2005, 22, 742;
5. Wu, Q.; Simons, C. Synthesis 2004, 1533;
6. Knapp, S. Chem. Rev. 1995, 95, 1859;
7. Harmange, J. C.; Figadere, B. Tetrahedron: Asymmetry 1993, 4, 1711.
8. Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348.
9. For reviews, see: (a) Kevin, D. A.; Meujo, D. A. F.; Hamann, M. T. Expert Opin. Drug Disc. 2009, 4, 109;
10. Nicolaou, K. C.; Frederick, M. O.; Aversa, R. J. Angew. Chem. 2008, 120, 7292.
11. Angew. Chem., Int. Ed. 2008, 47, 7182;
12. Satake, M. Top. Heterocycl. Chem. 2006, 5, 21;
13. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
14. For recent references, see: (a) Alvarez, O. C.; Salvatore, A.; Willink, E.; Ordonez, R.; Isla, M. I.; Neske, A.; Bardon, A. Nat. Prod. Commun. 2010, 5, 391;
15. Li, X.; Chen, X.-L.; Chen, J.-W.; Sun, D.-D. Chem. Nat. Compd. 2010, 46, 101;
16. Kojima, N.; Tanaka, T. Molecules 2009, 14, 3621;
17. McLaughlin, J. L. J. Nat. Prod. 2008, 71, 1311;
18. Nattrass, G. L.; Dez, E.; McLachlan, M. M.; Dixon, D. J.; Ley, S. V. Angew. Chem. 2005, 117, 586;
19. Angew. Chem., Int. Ed. 2005, 44, 580.
20. Saleem, M.; Kim, H. J.; Ali, M. S.; Lee, Y. S. Nat. Prod. Rep. 2005, 696.
21. Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407.
22. For reviews, see: (a) Furey, A.; Garcia, J.; O'Callaghan, K.; Lehane, M.; Amandi, M. F.; James, K. J. Phycotoxins 2007, 19;
23. Lvarez, E.; Candenas, M. L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953
24. Colby, E. A.; Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 4297;
25. Ghosh, A. K.; Liu, C. J. Am. Chem. Soc. 2003, 125, 2374;
26. Aissa, C.; Riveiros, R.; Ragot, J.; Forstner, A. J. Am. Chem. Soc. 2003, 125, 15512.
27. For reviews, see: (a) Wolfe, J. P.; Sassaman, M. B.; Kotian, K. D.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 1987, 52, 4314;
28. Wolfe, J. P.; Hay, M. B. Tetrahedron 2007, 63, 261;
29. Clarke, P. A.; Santos, S. Eur. J. Org. Chem. 2006, 2045;
30. Kilroy, T. G.; O'Sullivan, T. P.; Guiry, P. J. Eur. J. Org. Chem. 2005, 4929.
31. Lipinski, C.; Lombardo, D.; Dominy, B.; Feeney, P. Adv. Drug Delivery Rev. 1997, 23, 3;
32. Schreiber, S. L. Science 2000, 287, 1964;
33. Pelish, H. E.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740;
34. Schreiber, S. L. Chem. Eng. 2003, 3, 51.
35. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2,.
36. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
37. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
38. Son, S. U.; Yoon, Y. A.; Choi, D. S.; Park, J. K.; Kim, B. M.; Chung, Y. K. Org. Lett. 2001, 3, 1065;
39. Son, S. U.; Paik, S.-J.; Lee, S. I.; Chung, Y. K. J. Chem. Soc., Perkin Trans. 1 2000, 141;
40. Hong, S. H.; Kim, J. W.; Choi, D. S.; Chung, Y. K.; Lee, S.-G. J. Chem. Soc., Chem. Commun. 1999, 2099;
41. Son, S. U.; Choi, D. S.; Chung, Y. K. Org. Lett. 2000, 2, 2097;
42. Lee, S. I.; Son, S. U.; Choi, M. R.; Chung, Y. K.; Lee, S.-G. Tetrahedron Lett. 2003, 44, 4705;
43. Son, S. U.; Park, K. H.; Lee, S. J.; Kim, B. M.; Chung, Y. K. Synlett 2003, 1101;
44. Muto, R.; Ogasawara, K. Tetrahedron Lett. 2001, 42, 4143;
45. Tamao, K.; Kobayashi, T.; Ito, Y. Synlett 1992, 539.
46. Handbook of Asymmetric Heterogeneous Catalysis; Ding, K., Uozumi, Y., Eds.; Wiley-VCH: Weinheim, 2008.
47. Hydrolases in Organic Synthesis; Kazlauskas, R. J.; Bornscheuer, U. T., Eds., 2nd ed.; Wiley-VCH: Weinheim, 2006.
48. Tanyeli, C.; Demir, A. S.; Arkin, H.; Akhmedov, I. M. Enantiomer 1997, 2, 433;
49. Tanyeli, C.; Akhmedov, I. M.; Özdemirhan, D. Enantiomer 2001, 259.
50. Sezer, S.; Ozdemirhan, D.; Sahin, E.; Tanyeli, C. Tetrahedron: Asymmetry 2006, 17, 2981;
51. Sezer, S.; Şahin, E.; Tanyeli, C. Tetrahedron: Asymmetry 2010, 21, 476.
52. Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082.
53. Schreiber, S. L.; Burke, M. D. Angew. Chem. 2004, 43, 46;
54. Bergman, Y. E.; Mulder, R.; Perlmutter, P. J. Org. Chem. 2009, 74, 2589.
55. Sezer, S.; Gümrükçü, Y.; Şahin, E.; Tanyeli, C. Tetrahedron: Asymmetry 2008, 19, 2705.
56. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
57. Sing, S.; Kumar, S.; Chimni, S. Tetrahedron: Asymmetry 2002, 13, 2679.
58. Soderquist, A.; Lai, C. Org. Lett. 2005, 7, 799.