Synthesis of 2-(3-hydroxy-2-methyl-1-alkenyl)-1-pyrrolines and 2-(3-hydroxybutyl)-1-pyrroline using α-lithiated 2-methyl-1-pyrroline

Tetrahedron

Volumn 65, Issue 18, 2009, Pages 3753-3756

  D'hooghe, Matthias ^a   Abbaspour Tehrani, Kourosch ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 HYDROXY 2 METHYL 1 BUTENYL) 1 PYRROLINE; 2 (3 HYDROXY 2 METHYL 1 PROPENYL) 1 PYRROLINE; 2 (3 HYDROXYBUTYL) 1 PYRROLINE; LITHIUM DERIVATIVE; METHANOL; PYRROLINE DERIVATIVE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING;

EID: 63049130437     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.050     Document Type: Article

References (49)

1. For recent reviews, see:
2. Huang P.Q. Synlett (2006) 1133
3. Bellina F., and Rossi R. Tetrahedron 62 (2006) 7213
4. Pandey G., Banerjee P., and Gadre S.R. Chem. Rev. 106 (2006) 4484
5. Minatti A., and Muniz K. Chem. Soc. Rev. 36 (2007) 1142
6. Cheng X.C., Wang Q., Fang H., and Xu W.F. Curr. Med. Chem. 15 (2008) 374
7. For a few recent examples, see:
8. Torres-Sanchez M.I., Borrachero P., Cabrera-Escribano F., Gomez-Guillen M., Angulo-Alvarez M., Alvarez E., Favre S., and Vogel P. Tetrahedron: Asymmetry 18 (2007) 1809
9. Peng J., and Clive D.L.J. Org. Lett. 9 (2007) 2939
10. Behr J.-B., Gainvors-Claisse A., and Belarbi A. Nat. Prod. Res., Part A 21 (2007) 76
11. Behr J.-B., Gainvors-Claisse A., and Belarbi A. Nat. Prod. Res., Part B 20 (2006) 1308
12. Dürckheimer, W.; Martin, W.; Schrinner, E. Ger. Offen., 1974, DE 2319019;
13. Chem. Abstr. 82 (1975) 43170
14. Provot O., Celerier J.-P., Petit H., and Lhommet G. J. Org. Chem. 57 (1992) 2163
15. Provot O., Celerier J.-P., and Lhommet G. J. Heterocycl. Chem. 35 (1998) 371
16. Choi J.R., Han S., and Cha J.K. Tetrahedron Lett. 32 (1991) 6469
17. Cha, J. K.; Bennett, R. B., III. U.S. Patent 5,187,279 A;
18. Chem. Abstr. 118 (1993) 255177
19. Arai T., Abe H., Aoyagi S., and Kibayashi C. Tetrahedron Lett. 45 (2004) 5921
20. Dannhardt G., and Obergrusberger R. Arch. Pharm. 312 (1979) 498
21. Dannhardt G., and Obergrusberger R. Arch. Pharm. 312 (1979) 896
22. Böhme R., Rotscheidt K., and Breitmaier E. Synthesis (1989) 109
23. Schuster E., Hesse C., and Schumann D. Synlett (1991) 916
24. Dannhardt G., Lehr M., and Steindl L. Chem. Ztg. 110 (1986) 267
25. Dannhardt G., Meindl W., Gussmann S., Ajili S., and Kappe T. Eur. J. Med. Chem. 22 (1987) 505
26. Tirel P.J., Vaultier M., and Carrie R. Tetrahedron Lett. 30 (1989) 1947
27. Hua D.H., Bharathi S.N., Robinson P.D., and Tsujimoto A. J. Org. Chem. 55 (1990) 2128
28. Barluenga J., Tomas M., Kouznetsov V., and Rubio E. J. Chem. Soc., Chem. Commun. (1992) 1419
29. Bartoli G., Cimarelli C., Dalpozzo R., and Palmieri G. Tetrahedron 51 (1995) 8613
30. Dannhardt G., Bauer A., and Nowe U. J. Prakt. Chem. 340 (1998) 256
31. Fustero S., de la Torre M.G., Jofre V., Carlon R.P., Navarro A., Fuentes A.S., and Carrio J.S. J. Org. Chem. 63 (1998) 8825
32. Fustero S., de la Torre M.G., Pina B., and Fuentes A.S. J. Org. Chem. 64 (1999) 5551
33. Abbaspour Tehrani K., D'hooghe M., and De Kimpe N. Tetrahedron 59 (2003) 3099
34. Park K.-H., and Marshall W.J. J. Org. Chem. 70 (2005) 2075
35. Fustero S., Piera J., Sanz-Cervera J.F., Roman R., Brodsky B.H., Sanchez-Rosello M., Acena J.L., and Ramirez de Arellano C. Tetrahedron 62 (2006) 1444
36. Movassaghi M., and Chen B. Angew. Chem., Int. Ed. 46 (2007) 565
37. Stavinoha J., Bay E., Leone A., and Mariano P.S. Tetrahedron Lett. 21 (1980) 3455
38. Mariano P.S., Stavinoha J., and Bay E. Tetrahedron 37 (1981) 3385
39. Mangelinckx S., Giubellina N., and De Kimpe N. Chem. Rev. 104 (2004) 2353
40. Wittig G., Röderer R., and Fischer S. Tetrahedron Lett. 14 (1973) 3517
41. Muňoz O., Piovano M., Garbarino J., Hellwing V., and Breitmaier E. Phytochemistry 43 (1996) 709
42. Kim J.H., t'Hart H., and Stevens J.F. Phytochemistry 41 (1996) 1319
43. Schneider M.J., Brendze S., and Montali J.A. Phytochemistry 39 (1995) 1387
44. Gambaro V., Labbr C., and Castillo M. Phytochemistry 22 (1983) 1838
45. San Martin A., Rovirosa J., Gambaro V., and Castillo M. Phytochemistry 19 (1980) 2007
46. Christen P., Roberts M.F., Phillipson J.D., and Evans W.C. Phytochemistry 38 (1995) 1053
47. Chassot, L.; Braun, H.-J. Eur. Pat. Appl., 2007, EP 1752192 A1;
48. Chem. Abstr. 146 (2007) 235426
49. Gu X.P., Nishida N., Ikeda I., and Okahara M. J. Org. Chem. 52 (1987) 3192