Total synthesis of 3,4-dihydroxyprolines, D-threo-L-norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester

Tetrahedron Asymmetry

Volumn 14, Issue 24, 2003, Pages 3955-3963

  Soengas, Raquel G ^a   Estévez, Juan C ^a   Estévez, Ramón J ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3,4 DIHYDROXYTETRAHYDROFURAN 2 CARBOXYLIC ACID METHYL ESTER; 3,4 DIHYDROXYPROLINE; ACETIC ACID DERIVATIVE; ESTER DERIVATIVE; GLYCERALDEHYDE; NORVALINE; OXAMIC ACID; PROLINE DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ALDOL REACTION; ARTICLE; DIASTEREOISOMER; NITROSYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0345602140     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.10.005     Document Type: Article

References (50)

1. Henry C.R. Acad. Sci. Paris. 120:1895;1265.
2. Luzzio F.A. Tetrahedron. 57:2001;915 Noboru, O. In The Nitro Group in Organic Synthesis; Chapter 2. Organic Nitro Chemistry Series; Feuer, H., Ed.; Wiley-VCH: New York, 2001.
3. Luzzio F.A. Tetrahedron. 57:2001;915 Noboru, O. In The Nitro Group in Organic Synthesis; Chapter 2. Organic Nitro Chemistry Series; Feuer, H., Ed.; Wiley-VCH: New York, 2001.
4. Luzzio F.A. Tetrahedron. 57:2001;915 Noboru, O. In The Nitro Group in Organic Synthesis; Chapter 2. Organic Nitro Chemistry Series; Feuer, H., Ed.; Wiley-VCH: New York, 2001.
5. Pinnick H.W. Org. React. 38:1990;655.
6. McMurry J.E., Melton J., Padgett H. J. Org. Chem. 39:1974;259.
7. McMurry J.E., Melton J. J. Org. Chem. 38:1973;4367.
8. Olah G.A., Gupta B.G.B. Synthesis. 1980;44.
9. Crosslay M.J., Crumbie R.L., Fung Y.M., Potter J.J., Pegler M.A. Tetrahedron Lett. 28:1987;2883.
10. For reviews, see: (a) Schipchandler, M. T. Synthesis 1979, 666; (b) Shvekhgeimer, M. G. A. Russ. Chem. Rev. 1998, 67, 35; (c) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; (d) Rosini, G.; Ballini, R. Synthesis 1988, 833.
11. For reviews, see: (a) Schipchandler, M. T. Synthesis 1979, 666; (b) Shvekhgeimer, M. G. A. Russ. Chem. Rev. 1998, 67, 35; (c) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; (d) Rosini, G.; Ballini, R. Synthesis 1988, 833.
12. For reviews, see: (a) Schipchandler, M. T. Synthesis 1979, 666; (b) Shvekhgeimer, M. G. A. Russ. Chem. Rev. 1998, 67, 35; (c) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; (d) Rosini, G.; Ballini, R. Synthesis 1988, 833.
13. For reviews, see: (a) Schipchandler, M. T. Synthesis 1979, 666; (b) Shvekhgeimer, M. G. A. Russ. Chem. Rev. 1998, 67, 35; (c) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1; (d) Rosini, G.; Ballini, R. Synthesis 1988, 833.
14. Kaji E., Zen S. Bull. Chem. Soc. Jpn. 46:1973;337.
15. Shipchandler M.T. Synthesis. 1979;666.
16. Dauzonne D., Royer R. Synthesis. 1987;399.
17. Baldwin J.E., Haber S.B., Hoskins C., Kruse L.I. J. Org. Chem. 42:1977;1239.
18. Lalonde J.L., Bergbreiter D.E., Wong C.-H. J. Org. Chem. 53:1988;2323.
19. Keller E., Veldman N., Spek A.L., Feringa B.L. Tetrahedron: Asymmetry. 8:1997;3403.
20. Fornicola R.S., Oblinger E., Montgomery J. J. Org. Chem. 63:1998;3528.
21. Versleijen J.P.G., van Leusen A.M., Feringa B.L. Tetrahedron Lett. 40:1999;5803.
22. Fornicola R.S., Montgomery J. Tetrahedron Lett. 40:1999;8387.
23. Borrachero P., Dianez M.J., Estrada M.D., Gomez-Guillen M., Gomez-Sanchez A., Lopez-Castro A., Perez-Garrido S. Carbohydr. Res. 271:1995;79.
24. Soengas R.G., Estévez J.C., Estévez R.J., Maestro M.A. Tetrahedron: Asymmetry. 14:2003;1653.
25. Le Cocq J., Ballou C.E. Biochemistry. 3:1964;976.
26. Bock K., Lundt I., Pedersen C. Carbohydr. Res. 90:1981;17.
27. Hudson C.B., Roberston A.V., Simpson R.J. Aust. J. Chem. 21:1968;769.
28. Winchester B., Fleet G.W.J. Glycobiology. 2:1992;199.
29. Look G.C., Fotsch C.H., Wong C.-H. Acc. Chem. Res. 26:1993;182.
30. Fleet G.W.J., Karpas A., Dwek R.A., Fellows L.E., Tyms A.S., Petursson S., Namgoong S.K., Ramsden N.G., Smith P.W., Son J.C., Wilson F., Witty D.R., Jacob G.S., Rademacher T.W. FEBS Lett. 237:1988;128.
31. Kayakiri H., Nakamura K., Tagase S., Setoi H., Uchida I., Terano H., Hashimoto M., Tada T., Koga S. Chem. Pharm. Bull. 39:1991;2807.
32. For a recent use of 3,4-dihydroxyprolines as building blocks in peptide synthesis, see: Weir C.A., Taylor C.M. J. Org. Chem. 64:1999;1554.
33. Baird P.D., Dho J.C., Fleet G.W.J., Peach J.M., Prout K., Smith P.W. J. Chem. Soc., Perkin Trans. 1. 1987;1785.
34. Fuji M., Miura T., Kajimoto Y.I. Synlett. 2000;1046.
35. Lindblad W.J., Diegelmann R.F. J. Chromatogr. 315:1984;447.
36. Fowden L. Nature. 209:1966;807.
37. Matzinger P., Catalformo P., Eugster C.H. Helv. Chim. Acta. 55:1972;1478.
38. Pruess D.L., Kellet M. J. Antibiot. 36:1983;208.
39. Muller J.C., Toome V., Pruess D.L., Blount J.F., Weigele M. J. Antibiot. 36:1983;217.
40. Reading C., Cole M. Antimicrob. Agents Chemother. 11:1977;852.
41. DeBernardo S., Tengi J.T., Sasso G.J., Weigele M. J. Org. Chem. 50:1985;3457.
42. Ariza J., Díaz M., Font J., Ortuño R.M. Tetrahedron. 49:1993;1315.
43. Dondoni A., Marra A. Chem. Rev. 100:2000;4395. and references cited therein.
44. For the isolation of hydantocidin, see: (a) Harumayha, H.; Kinoshita, T. ; Takayama, T.; Kondo, M.; Nakajima, M.; Haneishi, T. J. Chem. Soc., Perkins Trans. 1 1991, 1637; (b) Nakajima, M.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okasaki, T.; Kawakubo, K.; Shindou, M.; Honma, T.; Tohjigamori, M.; Haneishi T. J. Antibiot. 1991, 44, 293.
45. For the isolation of hydantocidin, see: (a) Harumayha, H.; Kinoshita, T. ; Takayama, T.; Kondo, M.; Nakajima, M.; Haneishi, T. J. Chem. Soc., Perkins Trans. 1 1991, 1637; (b) Nakajima, M.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okasaki, T.; Kawakubo, K.; Shindou, M.; Honma, T.; Tohjigamori, M.; Haneishi T. J. Antibiot. 1991, 44, 293.
46. For the previous synthesis of amino acid 25, see: Hanessian S., Sancéau J.Y., Chemla P. Tetrahedron. 51:1995;6669.
47. Burton J.W., Son J.C., Fairbanks A.J., Choi S., Taylor H., Watkin D.J., Winchester B.G., Fleet G.W.J. Tetrahedron Lett. 34:1993;6119.
48. Estevez J.C., Burton J.W., Estevez R.J., Ardon H., Wormald M.R., Dwek R.A., Brown D., Fleet G.W.J. Tetrahedron: Asymmetry. 9:1998;2137.
49. Ghosh A.K., Koltun E.S., Bilcer G. Synthesis. 2001;1281.
50. Perrin D.D., Armarego W.L.F. Purification of Laboratory Chemicals. 1988;Pergamon Press, New York.