Amino and hydroxy acid based diastereoselective synthesis of 1- deoxygalactostatin and its imino acid derivative

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 2021-2024

  Ruiz, María ^a   Ruanova, Tania M ^a   Ojea, Vicente ^a   Quintela, José M ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYGALACTOSTATIN; 3,4,5 TRIHYDROXYPIPECOLIC ACID; GLYCINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; HYDROLYSIS; ION EXCHANGE CHROMATOGRAPHY; PROTON TRANSPORT; REVERSED PHASE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033525487     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00107-0     Document Type: Article

References (45)

1. a. Ganem. B. Acc. Chem. Res. 1996, 29, 340.
2. Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 153 and 661.
3. a. Miyake, Y.; Ebata, M. Agric. Biol. Chem. 1988, 52, 1649.
4. b. Legler, G.; Pohl, S. Carbohydr. Res. 1986, 155, 119.
5. Hettkamp, H.; Legler, G.; Bausse, E. Eur. J. Biochem. 1984, 142, 85.
6. Platt, F. M.; Neises, G.R.; Karlsson, G. B.; Dwek, R.A.; Butters, T. D. J. Biol. Chem. 1994, 269, 27108.
7. Elbein, A. D.; Kaushal, G. P. Methods Enzymol. 1994, 230, 316.
8. a. Gross, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935.
9. b. Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605.
10. c. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
11. Carbohydrate-based synthesis of : a. Paulsen, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. b. Bernotas, R. C.; Pezzonne, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. c. Heiker, F.-R.; Schueller, A. M. Carbohydr. Res.1990, 203, 314.
12. Carbohydrate-based synthesis of : a. Paulsen, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. b. Bernotas, R. C.; Pezzonne, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. c. Heiker, F.-R.; Schueller, A. M. Carbohydr. Res.1990, 203, 314.
13. Carbohydrate-based synthesis of : a. Paulsen, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601. b. Bernotas, R. C.; Pezzonne, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305. c. Heiker, F.-R.; Schueller, A. M. Carbohydr. Res. 1990, 203, 314.
14. d. Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3609.
15. e. Heightman, T. D.; Ermert, P.; Klein, D.; Vasella, A. Helv. Chim. Acta 1995, 78, 514.
16. f. Barili, P. L.; Berti, G.; Catelani, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407.
17. g. Shilvock, J. P.; Fleet, G. W. J. Synlett 1998, 554. See also reference 3b.
18. Non-carbohydrate-based routes to : a. Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1990, 56, 815. b. Liu, K. K.-C.; Kajimoto,T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. c. Lees, W. J.; Whitesides, G. M. Bioorg. Chem. 1992, 20, 173. d. Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 1247. e. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R.Tetrahedron Lett. 1995, 36, 653.
19. Non-carbohydrate-based routes to : a. Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1990, 56, 815. b. Liu, K. K.-C.; Kajimoto,T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. c. Lees, W. J.; Whitesides, G. M. Bioorg. Chem. 1992, 20, 173. d. Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 1247. e. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R.Tetrahedron Lett. 1995, 36, 653.
20. Non-carbohydrate-based routes to : a. Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1990, 56, 815. b. Liu, K. K.-C.; Kajimoto,T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. c. Lees, W. J.; Whitesides, G. M. Bioorg. Chem. 1992, 20, 173. d. Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 1247. e. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R.Tetrahedron Lett. 1995, 36, 653.
21. Non-carbohydrate-based routes to : a. Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1990, 56, 815. b. Liu, K. K.-C.; Kajimoto,T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. c. Lees, W. J.; Whitesides, G. M. Bioorg. Chem. 1992, 20, 173. d. Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 1247. e. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R.Tetrahedron Lett. 1995, 36, 653.
22. Non-carbohydrate-based routes to : a. Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1990, 56, 815. b. Liu, K. K.-C.; Kajimoto,T.; Chen, L.; Zhong, Z.; Ichikawa, Y.; Wong, C.-H. J. Org. Chem. 1991, 56, 6280. c. Lees, W. J.; Whitesides, G. M. Bioorg. Chem. 1992, 20, 173. d. Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1994, 1247. e. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. Tetrahedron Lett. 1995, 36, 653.
23. a. Ojea, V.; Ruiz, M; Quintela, J. M. Synlett 1997, 83.
24. b. Ruiz, M.; Ojea, V.; Quintela, J. M. Tetrahedron Lett. 1996. 37, 5743.
25. a. Majewski, M.; Shao, J.; Nelson, K.; Nowak, P.; Irvine, N. M. Tetrahedron Lett. 1998, 39, 6787.
26. b. Martin, S. F.; Chen, H.-J.; Lynch, V. M. J. Org. Chem. 1995, 60, 276.
27. c. Gallagher, T.; Giles, M.; Subramanian, S.; Hadley, M. S. J. Chem. Soc., Chem. Commun. 1992, 166.
28. d. Mukaiyama. T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265.
29. Williams, R. Synthesis of Optically Active α-amino Acids. Baldwin, J. E.; Magnus, P. D. Eds. Pergamon Press: Oxford 1989.
30. Grauert, M.; Schöllkopf, U. Liebigs Ann. Chem. 1985, 1817, and references cited therein. See also references 10 and 16.
31. a. Martin, S. F.; Chen, H.-J.; Yang, C.-P. J. Org. Chem. 1993, 58, 2867.
32. b. Mash, E. A.; Nelson, K. A.; Van Deusen, S., Hemperly, S. B. Org. Synth., Col. Vol VIII, 155. (-)-Dimethyl 2,3-O-isopropylidene L-tartrate is commercially available from Fluka.
33. (3R)-2,5-diethoxy-3-isopropyl-3,6-dihydropyrazine was prepared by treatment of cyclo[(2R)-val-gly] with triethyloxonium tetrafluoroborate. See Rose, J.E., Leeson, P.D.; Gani, D. J. Chem. Soc. Perkin Trans. 1 1995, 157. Alternatively, both enantiomers of the related 2,5-dimethoxy-3-isopropyl-3,6-dihydropyrazine can be purchased from E. Merck.
34. A Reunión Bienal de la Real Sociedad Espan̄ola de Química. Cádiz, September 1997 (ISBN 84-7786-458-6. vol 2, p. 1057).
35. Schöllkopf, U.; Nozulak, J.; Grauert, M. Synthesis 1985, 55.
36. The excess of Schöllkopf's reagent could be recovered, and showed no racemization.
37. 1H NMR spectrum of the mixture of adducts.
38. 2).
39. Kobayashi, S.; Furuta, T.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120. 908.
40. We have also observed an excellent diastereoselection in the additions of an excess of 7b to 2,3-O-isopropylidene-D-erythrose. Quintela, J. M.; Ruiz, M.; Ojea, V.; Ruanova, T. M., communication to the 18th ECHS. Rouen, France. September 1998.
41. See for example: Shilvock, J. P.; Whealley, J. R.; Davis, B.; Nash, R. J.; Griffiths, R. C.; Jones, M. G.; MÜller. M.; Crook, S.; Watkin, D. J.; Smith, C.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 8569.
42. 13C NMR and FABMS spectral data obtained for this material were also in accordance with the literature values (see references 8 and 9).
43. Tong, M. K.; Blumenthal, E. M.; Ganem, B. Tetrahedron Lett. 1990, 31, 1683. Other trihydroxypipecolic acids have shown important biological activities: Di Bello. I. C.; Dorling, P.; Fellows, L.; Winchester, B. FEBS Lett. 1984, 776, 61.
44. Tong, M. K.; Blumenthal, E. M.; Ganem, B. Tetrahedron Lett. 1990, 31, 1683. Other trihydroxypipecolic acids haveshown important biological activities: Di Bello. I. C.; Dorling, P.; Fellows, L.; Winchester, B. FEBS Lett. 1984, 776, 61.
45. 2O).