A straightforward synthesis of (2S,3R)-3-hydroxyproline and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 181-188

  Dell'Uomo, Natalina ^a,c   Di Giovanni, Maria Cristina ^a   Misiti, Domenico ^a   Zappia, Giovanni ^a   Delle Monache, Giuliano ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b CATHOLIC UNIVERSITY   (Italy)

^c Sigma Tau SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 2 HYDROXYMETHYLPROLINE; 3 HYDROXYPROLINE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

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

EID: 0030033716     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00434-3     Document Type: Article

References (39)

1. Sheehan, J. C.; Whitney, J. G. J. Am. Chem. Soc., 1962, 84, 3980.
2. Ko, C.; Johnson, L. D.; Priest, R. E. Biochem. Biophys. Acta, 1979, 581(2), 252.
3. Hoerrmann, W. Ger. Offen., DE 3,538, 619, 1986 [Chem. Abstr., 1986, 105, 120768].
4. Lubec, G. (Merckle G.m.b.H.), EP 307,390, 1989 [Chem. Abstr., 1990, 112, 215194].
5. Geissman, T. A.; Waiss, A.C., Jr. J. Org. Chem., 1962, 27, 139; Ikota, N.; Hanaki, A. Heterocycles, 1988, 27, 2535.
6. Geissman, T. A.; Waiss, A.C., Jr. J. Org. Chem., 1962, 27, 139; Ikota, N.; Hanaki, A. Heterocycles, 1988, 27, 2535.
7. Rueger, H.; Benn, M. Heterocycles, 1983, 20, 1331.
8. Li, W-R.; Han, S-Y.; Joullie, M. M. Tetrahedron, 1993, 49, 785.
9. Heffener, R. J.; Jiang, J.; Joullie, M. M. J. Am. Chem. Soc., 1992, 114, 10181.
10. Gardiner, R. A.; Rinehart, K. L., Jr., Snyder, J. J.; Broquist, H. P.; J. Am. Chem. Soc., 1968, 90, 5639.
11. Hohenschutz, L. D.; Bell, E. A.; Jewess, P. J.; Leworthy, D. P.; Pryce, R. J.; Arnold., E.; Clardy, J. Phytochemistry, 1981, 20(4), 811.
12. Molyneux, R. J.; Benson, M.; Wong, R. Y.; Tropea, J. E.; Elbein, A. D. J. Nat. Prod., 1988, 51(6), 1198.
13. Nash, R. J.; Fellows, L. E.; Dring, J. V.; Fleet, G. W. J.; Derome, A. E.; Hamor, T. A.; Scofield, A. M.; Watkin, D. J. Tetrahedron Lett., 1988, 29, 2487.
14. Nash, R. J.; Bell, E. A.; Fleet, G. W. J.; Jones, R. H.; Williams, J. M. J. Chem. Soc. Chem. Commun., 1985, 738.
15. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
16. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
17. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
18. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
19. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
20. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
21. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
22. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
23. Racemic 3-hydroxyproline: a) Morita, K.; Irreverre, F.; Sakiyama, F.; Witkop, B. J. Am. Chem. Soc., 1963, 85, 2832; b) Sheehan, J. C.; Whitney, J. G. ibid., 1963, 85, 1863-3865; c) J. Hausler, Liebigs Ann. Chem., 1981, 1073. [(2S,3R)-1]: d) Sundram, H.; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett., 1994, 35, 6975; e) Thaning, M.; Wistrand, L.-G. Acta Chem. Scand., 1989, 43, 290; [(2R,3S)-1]: f) Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett., 1993, 34, 7107; g) Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. ibid. 1990, 31, 4827; h) Roemmele, R. C.; Rapoport, H. J. Org. Chem., 1989, 54, 1866; i) Cooper, J.; Gallagher, P. T.; Knight, D. W. J. Chem. Soc. Chem. Commun., 1988, 509.
24. Griffart-Brunet, D.; Langlois, N. Tetrahedron Lett., 1994, 35, 119; Hirai, Y.; Chintani, M.; Yamazaki, T.; Momose, T. Chem. Letters, 1989, 1449.
25. Griffart-Brunet, D.; Langlois, N. Tetrahedron Lett., 1994, 35, 119; Hirai, Y.; Chintani, M.; Yamazaki, T.; Momose, T. Chem. Letters, 1989, 1449.
26. a) Di Giovanni, M. C.; Misiti, D.; Zappia, G.; Delle Monache, G. Tetrahedron, 1993, 49, 11321;
27. b) Dell'Uomo, N.; Di Giovanni, M. C.; Misiti, D.; Zappia, G.; G. Delle Monache, Liebigs Ann. Chem. 1994, 641.
28. Delle Monache, G.; Di Giovanni, M. C.; Maggio, F.; Misiti, D.; Zappia, G. Synthesis, in press.
29. Soai, K.; Oyamada, H.; Takase, M. Bull. Chem. Soc. Japn., 1984, 57, 2327.
30. Alper, R. Angew. Chem. Int. Ed., 1975, 14, 801; Castro, B. R. Org. Reactions, 1983, 29, 1.
31. Alper, R. Angew. Chem. Int. Ed., 1975, 14, 801; Castro, B. R. Org. Reactions, 1983, 29, 1.
32. Takahata, H.; Banba, Y.; Tajima, M.; Momose, T. J. Org. Chem., 1991, 56, 240-245.
33. Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett., 1992, 33, 5029.
34. Abiko, A.; Roberts, J. C.; Takemasa, T.; Masamune, S. Tetrahedron Lett., 1986, 27, 4537.
35. Mitsunobu, O. Synthesis, 1981, 1; Hughes, D. L. Org. Reactions, 1992, 42, 335.
36. Mitsunobu, O. Synthesis, 1981, 1; Hughes, D. L. Org. Reactions, 1992, 42, 335.
37. Martin, S. F.; Dodge, J. A. Tetrahedron Lett., 1991, 32, 3017.
38. Stahl, G. L.; Walter, R.; Smith, C. W. J. Org. Chem., 1978, 43, 2285.
39. D.D. Perrin, W. L. Armarego, Purification of Laboratory Chemicals, Pergamon Press, Oxford, 1988.