Enantioselective synthesis of (2R,4S)- and (2S,4R)-4-hydroxypipecolic acid from D-glucoheptono-1,4-lactone

Journal of Organic Chemistry

Volumn 64, Issue 17, 1999, Pages 6119-6125

  Di Nardo, Christián ^a   Varela, Oscar ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIDEOXY DEXTRO XYLO HEPTONO 1,4 LACTONE; 4 HYDROXYPIPECOLIC ACID; DEXTRO GLUCOHEPTONO 1,4 LACTONE; LACTONE DERIVATIVE; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; HYDROLYSIS; OXIDATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033588134     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990445+     Document Type: Article

References (35)

1. (a) Romeo, J. T.; Swain, L. A.; Bleecker, A. B. Phytochemistry 1983, 22, 1615.
2. (b) Schenk, V. W.; Schutte, H. R. Flora 1963, 153, 426.
3. Vanderhaeghe, H.; Janssen, G.; Compernolle, F. Tetrahedron Lett. 1971, 28, 2687.
4. Hays, S. J.; Malone, T. C.; Johnson, G. J. Org. Chem. 1991, 56, 4084 and references therein.
5. (a) Beaulieu, P. L.; Lavallée, P.; Abraham, A.; Anderson, P. C.; Boucher, C.; Bousquet, Y.; Duceppe, J.-S.; Gillard, J.; Gorys, V.; Grand-Maitre, C.; Grenier, L.; Guindon, Y.; Guse, I.; Plamondom, L.; Soucy, F.; Valois, S.; Wernic, D.; Yoakim, C. J. Org. Chem. 1997, 62, 3440.
6. (b) Anderson, P. C.; Soucy, F., Yoakim, C.; Lavallée, P.; Beaulieu, P. L. U.S. Patent 5 614 533, 1997; Chem. Abstr. 1997, 126, 305785v.
7. (a) Barluenga, J.; Aznar, F.; Valdés, C.; Ribas, C. J. Org. Chem. 1998, 63, 3918.
8. (b) Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549.
9. (c) Holmes, A. B.; Swithenbank, C.; Williams, S. F. J. Chem. Soc., Chem. Commun. 1986, 265.
10. (d) Herdeis, C.; Nagel, U. Heterocycles 1983, 20, 2163.
11. Nin, A. P.; Varela, O.; de Lederkremer, R. M. Tetrahedron 1993, 49, 9459.
12. Orstein, P. L.; Schoepp, D. D.; Arnold, M. B.; Leander, J. D.; Lodge, D.; Paschal, J. W.; Elzey, T. J. Med. Chem. 1991, 34, 90.
13. (a) Each, P. M.; de Boer, R. F.; Hiemstra, H.; Boska, I. M.; Speckamp, W. N. Tetrahedron 1991, 47, 4063.
14. (b) Each, P. M.; Boska, I. M.; Hiemstra, H.; Speckamp, W. N. Synlett 1989, 38.
15. Clark-Lewis, J. W.; Mortimer, P. I. J. Chem. Soc. 1961, 189.
16. Hartmann, P.; Obrecht, J.-P. Synth. Commun. 1988, 18, 553.
17. Jackson, R. F. W.; Graham, L. J.; Rettie, A. B. Tetrahedron Lett. 1994, 35, 4417.
18. Golubev, A.; Sewald, N.; Burger, K. Tetrahedron Lett. 1995, 36, 2037.
19. Jolles, G.; Poiget, G.; Robert, J.; Terlain, B.; Thomas, J.-P. Bull. Soc. Chim. Fr. 1965, 2252.
20. Gillard, J.; Abraham, A.; Anderson, P. C.; Beaulieu, P. L.; Bogri, T.; Bousquet, Y.; Grenier, L.; Guse, I.; Lavallée, P. J. Org. Chem. 1996, 61, 2226.
21. Di Nardo, C.; Jeroncic, L. O.; de Lederkremer, R. M.; Varela, O. J. Org. Chem. 1996, 61, 4007.
22. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley: New York, 1991; pp 127-128.
23. (a) Varela, O.; Nin, A. P.; de Lederkremer, R. M. Tetrahedron Lett. 1994, 35, 9359.
24. (b) Marino, M. C.; Varela, O.; de Lederkremer, R. M. Carbohydr. Res. 1991, 220, 145.
25. (c) Moradei, O.; du Mortier, C.; Varela, O.; de Lederkremer, R. M. J. Carbohydr. Chem. 1991, 10, 469.
26. Hussain, S. A. M. T.; Ollis, W. D.; Smith, C.; Stoddart, J. F.J. Chem. Soc., Perkin Trans. 1 1975, 1480.
27. 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.
28. Shing, T. K. M.; Zhong, Y.-L. J. Org. Chem. 1997, 62, 2662.
29. Wu, W.-L.; Wu, Y.-L. J. Org. Chem. 1993, 58, 3586.
30. (a) Bashyal, B. P.; Chow, H.-F.; Fellows, L. E.; Fleet, G. W. J. Tetrahedron 1987, 43, 415.
31. (b) Bashyal, B. P.; Chow, H.-F.; Fleet, G. W. J. Tetrahedron 1987, 43, 423.
32. (c) Bashyal, B. P.; Fleet, G. W. J.; Gough, M. J.; Smith, P. W. Tetrahedron 1987, 43, 3083.
33. Varela, O.; Zunszain, P. A. J. Org. Chem. 1993, 58, 7860.
34. (a) Johnson, R. L.; Rajakumar, G.; Mishra, R. M. J. Med. Chem. 1986, 29, 2100.
35. 1H FT NMR Spectra; Aldrich: Milwaukee, 1992; Vol. 1, pp 889 A-C, 1085 B.