Synthesis of trehazolin from D-glucose

Journal of Organic Chemistry

Volumn 63, Issue 17, 1998, Pages 5877-5882

  Boiron, Arnaud ^a   Zillig, Peter ^a   Faber, Dominik ^a   Giese, Bernd ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; ENZYME INHIBITOR; ETHER DERIVATIVE; GLUCOSE; OXIME; TREHALASE; TREHAZOLAMINE; TREHAZOLIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032555461     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980485y     Document Type: Article

References (56)

1. Elbein, A. D. Adv. Carbohydr. Chem. Biochem. 1974, 30, 227.
2. Ando, O.; Satake, H.; Itoi, K_; Sato, A.; Nakajima, M.; Takahashi, S.; Haruyama, H.; Ohkuma, Y.; Kinoshita, T.; Enokita, R. J. Antibiot. 1991, 44, 1165.
3. (a) Ogawa, S.; Uchida, C. Chem. Lett. 1993, 173.
4. (b) Uchida, C.; Yamagishi, T.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 589.
5. (c) Ledford, B. E.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 11811.
6. (d) Kobayashi, Y.; Miyazaki, H.; Shiozaki, M. J. Org. Chem. 1994, 59, 813.
7. (e) Ogawa, S.; Uchida, C. J. Chem. Soc., Perkin Trans. 1 1992, 1939.
8. (a) Kobayashi, Y.; Shiozaki, M. J. Org. Chem. 1995, 60, 2570.
9. (b) Uchida, C.; Ogawa, S. Carbohydr. Lett. 1994, 1, 77.
10. (c) Uchida, C.; Yamagishi, T.; Kitahashi, H.; Iwaisaki, Y.; Ogawa, S. Bioorg. Med. Chem. 1995, 3, 1605.
11. (d) Uchida, C.; Ogawa, S. Bioorg. Med. Chem. 1996, 4, 275.
12. (e) Uchida, C.; Kitahashi, H.; Yamagishi, T.; Iwaisaki, Y.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1994, 2775.
13. (f) Uchida, C.; Kitahashi, H.; Watanabe, S.; Ogawa, S. J. Chem. Soc., Perkin Trans. 1 1995, 1707.
14. Camarasa, M. J.; Fernández-Resa, P.; García-López, M. T.; De las Heras, F. G.; Méndez-Castrillón, P. P.; San Felix, A. Synthesis 1984, 509.
15. (a) Ogawa, S.; Uchida, C.; Yuming, Y. J. Chem. Soc., Chem. Commun. 1992, 886.
16. (b) Knapp, S.; Purandare, A.; Rupitz, K.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 7461.
17. To our knowledge the biosynthesis of trehazolin (2) is not known.
18. (a) Giese, B.; Kopping, B.; Goebel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K.; Trach, F. Org. React. (N.Y.) 1996, 48, 301.
19. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: New York 1996; Chapter 2.
20. (a) Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1995, 117, 7283.
21. (b) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
22. (c) Uenishi, J.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097.
23. (d) Chiara, J. L.; Valle, N. Tetrahedron: Asymmetry 1995, 6, 1895.
24. (e) Chiara, J. L.; Martín-Lomas, M. Tetrahedron Lett. 1994, 35, 2969.
25. (f) Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125.
26. (g) Guidot, J. P.; Le Gall, T.; Mioskowski, C. Tetrahedron Lett. 1994, 36, 6671.
27. (h) Carpintero, M.; Fernández-Mayoralas, A.; Jaramillo, C. J. Org. Chem. 1997, 62, 1916.
28. (i) Wirth, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 61.
29. (j) Adinolfi, M.; Barone, G.; Iadonisi, A.; Mangoni, L. Tetrahedron Lett. 1998, 39, 2021.
30. (k) Chiara, J. L. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998; Chapter 7.
31. (a) Kiguchi, T.; Tajiri, K.; Ninomiya, I.; Naito, T.; Hiramatsu, H. Tetrahedron Lett. 1995, 36, 253.
32. (b) Chiara, J. L.; Marco-Contelles, J.; Khiar, N.; Gallego, P.; Destabel, C.; Bernabé, M. J. Org. Chem. 1995, 60, 6010.
33. (c) Naito, T.; Tajiri, K.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett. 1994, 35, 2205.
34. (d) Marco-Contelles, J.; Gallego, P.; Rodríguez-Fernández, M.; Khiar, N.; Destabel, C.; Bernarbé, M.; Martínez-Grau, A.; Chiara, J. L. J. Org. Chem. 1997, 62, 7397, and references therein.
35. (e) Tormo, J.; Hays, D. S.; Fu, G. J. Org. Chem. 1998, 63, 201.
36. (f) Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543.
37. 10d almost only 13b was obtained. Thus, the nature of the metal and not that of the oxime ether seems to determine the selectivity of the coupling.
38. (a) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447.
39. (b) Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514.
40. (a) Wu, Y.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1656.
41. (b) Inanaga, J.; Katsuki, J.; Ujikawa, O.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 4921.
42. Qiao, L.; Veredas, J. C. J. Org. Chem. 1993, 58, 3480.
43. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899, and references therein.
44. 3SnH/ AIBN in refluxing benzene a mixture of products 17 and its epimer at the quaternary center epi-17 were obtained (see Experimental Section).
45. See Supporting Information.
46. Using carbohydrate numbering.
47. The use of most oxidizing agents resulted in formation of compound 16.
48. (a) Norman, R. O. C.; Purchase, R.; Thomas, C. B. J. Chem. Soc., Perkin Trans. 1 1972, 1701.
49. (b) Weiss, R. H.; Furfine, E.; Hausleden, E.; Dixon, D. W. J. Org. Chem. 1984, 49, 4969.
50. 3, TEMPO or NaOCl failed.
51. In the absence of MeONa, the reaction was messy.
52. Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525.
53. Reference plane: paper sheet; molecule as depicted in Scheme 5.
54. D = +1.7 (c 0.41, MeOH)) is very low.
55. For more details see Supporting Information.
56. D, IR, TLC).