Stereoselective synthesis of five and/or six membered ring hydroxylactones obtained by Lewis acid mediated reaction of γ,δ-epoxy-β-hydroxyesters; access to 5-methylated 2-deoxysugars

Tetrahedron

Volumn 53, Issue 2, 1997, Pages 659-672

  Nacro, Kassoum ^a   Baltas, Michel ^a   Escudier, Jean Marc ^a   Gorrichon, Liliane ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

furanosides; lactonisation; optically active , epoxy hydroxyesters

Indexed keywords

CARBOHYDRATE DERIVATIVE; LACTONE DERIVATIVE; POLYOL;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031012715     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00998-2     Document Type: Article

References (53)

1. a) Wuts, P.G.M.; D'Costa, R.; Butler W. J. Org. Chem. 1984, 49, 2582-2588.
2. b) Paterson, I.; Boddy, I.; Mason, I. Tetrahedron Lett. 1987, 28, 5205-5208.
3. c) Paterson, I.; Boddy, I. Tetrahedron Lett. 1988, 29, 5301-5304.
4. d) Paterson, I.; Tillyer, R.D.; Smaill, J.B. Tetrahedron Lett. 1993, 34, 7137-7140.
5. a) Mori, K.; Ueda, H.; Tetrahedron 1981, 37, 2581-2583.
6. b) Richards, R.W.; Thomas, R.D. Tetrahedron Lett. 1992, 33, 8137-8140.
7. a) Hashimoto, M.; Kan, T.; Nozaki, K.; Yanagiya, M.; Shirahama, H.; Matsumoto, T. J. Org. Chem. 1990, 55, 5088-5107.
8. b) Corey, E.J.; Ha, D.-C. Tetrahedron Lett. 1988, 29, 3171-3174.
9. c) Alcaray, L.; Harnett, J.J.; Miokowski, C.; Le Gall, T.; Shin, D.-S.; Folck, J.R. J. Org. Chem. 1995, 60, 7209-7214.
10. d) Jung, M.E.; Lew, W. J. Org. Chem. 1991, 56, 1347-1349.
11. e) Jung, M.E.; D'Amico, D.C.; Lew, W. Tetrahedron Lett. 1993, 34, 923-926.
12. f) Urones, J.G.; Diez, D.; Marcos, I.S.; Basabe, P.; Lithgow, A.M.; Moro, R.F.; Garrido, N.M.; Escarcena, R. Tetrahedron 1995, 51, 3691-3704.
13. Ohfune, Y.; Hori, K.; Sakaitani, M. Tetrahedron Lett. 1986, 27, 6079-6082.
14. a) Chamberlin, A. R.; Dezube, M.; Reich, S. H.; Sall, D. J. J. Am. Chem. Soc. 1989, 111, 6247-6256.
15. b) Hanessian, S.; Murray, P. J.; Sahoo, S. P. Tetrahedron Lett. 1985, 26, 5623-5626; 5627-5630; 5631-5634.
16. Posner, G. H.; Kogan, T. P.; Haines, S. R.; Frye, L. L. Tetrahedron Lett. 1984, 25, 2627-2630.
17. Vigneron, J. P.; Meric, R.; Larchevêque, M.; Debal, A.; Lallemand, J. Y.; Kunesch, G.; Zagatti, P.; Gallois, M. Tetrahedron 1984, 40, 3521-3529.
18. a) Paquette, L. A.; Rayner, C. M.; Doherty, A. M. J. Am. Chem. Soc. 1990, 112, 4078-4079.
19. b) Ortuno, R. M.; Merce, R.; Font, J. Tetrahedron 1987, 43, 4497-4506.
20. Nacro, K.; Baltas, M.; Escudier, J.-M.; Gorrichon, L. Tetrahedron Lett. 1995, 33, 7867-7870.
21. Saha, A.K.; Caulfield, T.J.; Hobbs, C.; Upson, D.A.; Waychunas, C.; Yawman, A.M. J. Org. Chem. 1995, 60, 788-789.
22. a) Scheuer-Larsen, C.; Pfundheller, H.M.; Wengel, J. J. Org. Chem. 1995, 60, 7298-7303.
23. b) Hiebl, J.; Zbiral, E.; Balzarini , J.; De Clercq, E. J. Med. Chem. 1992, 35, 3016-3023 and references cited therein.
24. a) Escudier, J. M.; Baltas, M.; Gorrichon, L. Tetrahedron 1993, 49, 5253-5266.
25. b) Escudier, J. M.; Baltas, M.; Gorrichon, L. Tetrahedron Lett. 1992, 33, 1439-1442.
26. Nacro, K.; Baltas , M.; Escudier, J.-M.; Gorrichon, L. Tetrahedron 1996, 52, 9047-9056.
27. 3, Z = 4, F(000) = 496. Data collected on a CAD4 Enraf-Nonius diffractometer at room temperature using graphite monochromated Mo-Kα radiation. 771 unique reflexions were collected in the range 0 ≤ θ ≤ 29°. The structure was solved by the shelxs method. The final residuals were R = 0.0592 and Rw = 0.0590. Atomic coordinates bond lengths and angles and thermal parameters have been deposited at the Cambridge Cristallographic Data centre.
28. a) Cornforth, D. A.; Opara, A. E.; Read, G. J. Chem. Soc. (C) 1969, 2799-2805.
29. b) Opara, A.E.; Read, G. J. C. S. Chem. Commun., 1969, 679.
30. c) Baltas, M.; Cazaux, L.; De Blic, A.; Gorrichon, L.; Tisnès, P.; Touati, A. Bull. Soc. chim. Fr. 1988, 79-87.
31. d) Baltas, M.; Cazaux, L.; De Blic, A.; Gorrichon, L.; Tisnès, P. J. Chem. Research 1988, 284-285(S), 2236-2261(M).
32. a) Paterson, I.; Craw, P. A. Tetrahedron Lett. 1989, 50, 5799-5802.
33. b) Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1985, 107, 1691-1694.
34. a) Brown, J. M.; Conn, A. D.; Pilcher, G.; Leitao, M. L. P.; Meng-Yan, Y. J. C. S. Chem. Commun. 1989, 1817-1819.
35. b) Isaac, I.; Stasik, I.; Beaupère, D.; Uzan, R. Tetrahedron Lett. 1995, 36, 383-386.
36. a) Mulholland, R.L. Jr.; Chamberlin, A.R. J. Org. Chem. 1988, 53, 1082-1085.
37. b) Fotsch, C.H.; Chamberlin, A.R. J. Org. Chem. 1991, 56, 4141-4147.
38. c) Evans, D.A.; Polniasycky, R.P.; De Vries, K.M.; Guinn, D.E.; Mathre, D.J. J. Am. Chem. Soc. 1991, 113, 7613-7630.
39. d) Han, S.Y.; Joullie, M.M.; Fokin, V.V.; Petasis, N.A. Tetrahedron Asym., 1984, 5, 2535-2562.
40. a) Baldwin, J. E. J. C. S. Chem. Commun. 1976, 734-736.
41. b) Baldwin, J. E.; Thomas, R. C.; Kruse, L. I.; Sikberman, L. J. Org. Chem. 1977, 42, 3846-3852.
42. a) Nicolaou, K.C.; Duggan, M.E.; Hwang, C.-K.; Somers, P.K. J. C. S. Chem. Commun. 1985, 1359-1362.
43. b) Nicolaou, K.C.; Prasad, C.V.C.; Hwang, C.-K.; Duggan, M.E.; Veale, C.A. J. Am. Chem. Soc. 1989, 111, 5321-5330.
44. c) Nicolaou, K.C.; Prasad, C.V.C.; Somers, P.K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330-5334.
45. d) Nicolaou, K.C.; Prasad, C.V.C.; Somers, P.K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5335-5340.
46. a) Harmange, J. C.; Figadere, B. Tetrahedron Asym. 1993, 4, 1711-1754.
47. b) Chamberlin, A. R.; Dezube, M.; Reich, S. H.; Sall, D. J. J. Am. Chem. Soc. 1989, 111, 6247-6256.
48. Chamberlin, A. R.; Dezube, M.; Dussault, P; Mc Mills, M. C. J. Am. Chem. Soc. 1983, 705, 5819-5825.
49. Beachmam, A.R.; Bruce, I.; Choi, S.; Doherty, O.; Fairbanks, A.J.; Fleet, G.W.J.; Skeat, B.M.; Paech, J.M.; Saunders, J.; Watkin, D.J. Tetrahedron Asym 1991, 2, 883-900; 901-912.
50. Han, S.Y.; Joullié, M.M.; Fokin, V.V.; Petasis, M. A. Tetrahedron Asym. 1994, 5, 2535-2562 and references therein.
51. Teng, K.; Marquez, V.E.; Milne, G.W.A.; Barchi Jr, J.J.; Kazanietz, M.G.; Lewin, N.E.; Blumberg, P.M.; Abushanab, E. J. Am. Chem. Soc. 1992, 114, 1059-1070.
52. Yamazaki, T.; Mitzutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346-4359.
53. Kobayashi, S.; Onazawa, S.-Y.; Mukaiyama, T. Chem Lett. 1992, 2419-2422.