An efficient stereoselective synthesis of (3S,4R)-4-(hydroxymethyl) pyrrolidin-3-ol from (S)-diethylmalate

Tetrahedron Letters

Volumn 46, Issue 19, 2005, Pages 3327-3330

  Kotian, Pravin L ^a   Chand, Pooran ^a  

^a BIOCRYST PHARMACEUTICALS INC   (United States)

Author keywords

Diethylmalate; Imino sugar

Indexed keywords

BCX 4208; ENZYME INHIBITOR; IMMUCILLIN H; MALIC ACID DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 17144428058     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.077     Document Type: Article

References (30)

1. M. Bols, and S.U. Hansen Acta Chem. Scand. 52 1998 1214 1222
2. G. Limberg, I. Lundt, and J. Zavilla Synthesis 1999 178 183
3. M.D. Sorensen, N.M. Khalifa, and E.B. Pedersen Synthesis 1999 1937 1943
4. P. Thorbek, H. Hjeds, and K. Schaumburg Acta Chem. Scand. Ser. B 35 1981 473 479
5. J.P. Jacquet, D. Bouzard, J.-R. Kiechel, and P. Remuzon Tetrahedron Lett. 32 1991 1565 1568
6. D. Bouzard, P. Di Cesare, M. Essiz, J.P. Jacquet, J.-R. Kiechel, P. Remuzon, A. Weber, T. Oki, M. Masuyoshi, R.E. Kessler, J. Fung-Tomc, and J. Desiderio J. Med. Chem. 33 1990 1344 1352
7. C.M. Li, P.C. Tyler, R.H. Furneaux, G. Kicska, Y. Xu, C. Grubmeyer, M.E. Girven, and V.L. Schramm Nat. Struct. Biol. 6 1999 582 587
8. G.B. Evans, R.H. Furneaux, G.J. Gainsford, V.L. Schramm, and P.C. Tyler Tetrahedron 56 2000 3053 3062
9. G.A. Kicska, L. Long, H. Hörig, C. Fairchild, P.C. Tyler, R.H. Furneaux, V.L. Schramm, and H.L. Kaufman Proc. Natl. Acad. Sci. U.S.A. 98 2001 4593 4598
10. G.A. Kicska, P.C. Tyler, G.B. Evans, R.H. Furneaux, K. Kim, and V.L. Schramm J. Biol. Chem. 277 2002 3219 3225
11. G.B. Evans, R.H. Furneaux, G.J. Gainsford, J.C. Hanson, G.A. Kicska, A.A. Sauve, V.L. Schramm, and P.C. Tyler J. Med. Chem. 46 2003 155 160
12. V.L. Schramm, and P.C. Tyler Curr. Top. Med. Chem. 3 2003 525 540
13. G.B. Evans, R.H. Furneaux, P.C. Tyler, and V.L. Schramm Org. Lett. 5 2003 3639 3640
14. G.B. Evans, R.H. Furneaux, A. Lewandowicz, V.L. Schramm, and P.C. Tyler J. Med. Chem. 46 2003 5271 5276
15. E. Jaeger, and J.H. Biel J. Org. Chem. 30 1965 740 744
16. K. Makino, and Y. Ichikawa Tetrahedron Lett. 39 1998 8245 8248
17. V.V. Filichev, and E.B. Pederson Tetrahedron 57 2001 9163 9168
18. V.V. Filichev, M. Brandt, and E.B. Pederson Carbohydr. Res. 333 2001 115 122
19. S. Karlsson, and H.-E. Hogberg Tetrahedron: Asymmetry 12 2001 1977 1982
20. S. Karlsson, and H.-E. Hogberg Org. Lett. 1 1999 1667 1669
21. P.L. Kotian, T.-H. Lin, Y. El-Kattan, and P. Chand Org. Proc. Res. Dev. 2 2005 193 197
22. M. Godskesen, and I. Lundt Tetrahedron Lett. 39 1998 5841 5844
23. T. Ueki, Y. Morimoto, and T. Kinoshita Chem. Commun. 2001 1820 1821
24. A.I. Meyers, J.P. Lawson, D.G. Walker, and R.J. Linderman J. Org. Chem. 51 1986 5111 5123
25. 7) C, H. [ α ] D 25 -38.15 (c 1.28, acetone)
26. 2O) C, H. [ α ] D 25 -7.5 (c 1.45, acetone)
27. 2) C, H. [ α ] D 25 -4.37 (c 1.15, ethanol)
28. 3) C, H, N. [ α ] D 25 -8.6 (c 1.17, ethanol)
29. 2•HCl) C, H, N. [ α ] D 25 -19.8 (c 0.61, methanol)
30. 22 [ α ] D 25 -10.2 (c 0.6, methanol)