Direct stereoselective synthesis of enantiomerically pure anti -β-amino alcohols

Journal of Organic Chemistry

Volumn 79, Issue 15, 2014, Pages 6775-6782

  Silveira Dorta, Gastón ^a   Donadel, Osvaldo J ^b   Martín, Víctor S ^a   Padrón, José M ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; ENANTIOMERS; ESTERS; STEREOCHEMISTRY;

ALPHA-AMINO ACIDS; BENZYL ESTERS; FREE HYDROXYL GROUPS; GRIGNARD REAGENT; SEQUENTIAL REDUCTIONS; SPHINGANINE; STEREOSELECTIVE SYNTHESIS;

STEREOSELECTIVITY;

2 (DIBENZYLAMINO) 1 PHENYLPENTAN 3 OL; 2 (DIBENZYLAMINO)PENT 4 ENE 1,3 DIOL; 2 (DIBENZYLAMINO)PENT 4 YNE 1,3 DIOL; 2 (DIBENZYLAMINO)PENTAN 3 OL; 2 (DIBENZYLAMINO)PENTANE 1,3 DIOL; 2 AMINO 1 PHENYLPENTAN 3 OL; 2 AMINOPENTAN 3 OL; 3 (DIBENZYLAMINO)HEX 5 ENE 1,4 DIOL; 3 (DIBENZYLAMINO)HEX 5 ENE 2,4 DIOL; 3 (DIBENZYLAMINO)HEX 5 YNE 1,4 DIOL; 3 (DIBENZYLAMINO)HEX 5 YNE 2,4 DIOL; 3 (DIBENZYLAMINO)HEXANE 1,4 DIOL; 3 (DIBENZYLAMINO)HEXANE 2,4 DIOL; 4 (DIBENZYLAMINO) 5 ETHYLDIHYDROFURAN 2(3H) ONE; 4 (DIBENZYLAMINO) 5 ETHYNYLDIHYDROFURAN 2(3H) ONE; 4 (DIBENZYLAMINO) 5 PHENYLPENT 1 EN 3 OL; 4 (DIBENZYLAMINO) 5 PHENYLPENT 1 YN 3 OL; 4 (DIBENZYLAMINO) 5 VINYLDIHYDROFURAN 2(3H) ONE; 4 (DIBENZYLAMINO)PENT 1 EN 3 OL; 4 (DIBENZYLAMINO)PENT 1 YN 3 OL; ALCOHOL DERIVATIVE; AMINOALCOHOL; ANTI BETA AMINO ALCOHOL; N,N DIBENZYL 2,2 DIMETHYL 4 VINYL 1,3 DIOXAN 5 AMINE; N,N DIBENZYL 2,2,4 TRIMETHYL 6 VINYL 1,3 DIOXAN 5 AMINE; N,N DIBENZYL 4 ETHYL 2,2 DIMETHYL 1,3 DIOXAN 5 AMINE; N,N DIBENZYL 4 ETHYL 2,2,6 TRIMETHYL 1,3 DIOXAN 5 AMINE; N,N DIBENZYL 4 ETHYNYL 2,2 DIMETHYL 1,3 DIOXAN 5 AMINE; N,N DIBENZYL 4 ETHYNYL 2,2,6 TRIMETHYL 1,3 DIOXAN 5 AMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; ALDEHYDE; AMINO ACID; SAFINGOL; SPHINGOSINE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; NUCLEOPHILICITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; AMINO ACIDS; AMINO ALCOHOLS; MOLECULAR STRUCTURE; SPHINGOSINE; STEREOISOMERISM;

EID: 84905392423     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500481j     Document Type: Article

References (59)

1. Anaya de Parrodi, C.; Juaristi, E. Synlett 2006, 2699
2. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835
3. Métro, T.-X.; Gomez-Pardo, D.; Cossy, J. J. Org. Chem. 2008, 73, 707
4. Weinstein, A. B.; Schuman, D. P.; Tan, Z. X.; Stahl, S. S. Angew. Chem., Int. Ed. 2013, 52, 11867
5. Bergmeier, S. C. Tetrahedron 2000, 56, 2561
6. Choi, J.-H.; Yoshida, M.; Suzuki, T.; Harada, E.; Kawade, M.; Yazawa, K.; Nishimoto, S.; Hirai, H.; Kawagishi, H. Tetrahedron 2013, 69, 8609
7. Abad, J. L.; Nieves, I.; Rayo, P.; Casas, J.; Fabriàs, G.; Delgado, A. J. Org. Chem. 2013, 78, 5858
8. Menna, M. Phytochem. Rev. 2009, 8, 461
9. Padrón, J. M. Curr. Med. Chem. 2006, 13, 755
10. Aiello, A.; Fattorusso, E.; Giordano, A.; Menna, M.; Navarrete, C.; Muñoz, E. Bioorg. Med. Chem. 2007, 15, 2920
11. Aiello, A.; Fattorusso, E.; Giordano, A.; Menna, M.; Navarrete, C.; Muñoz, E. Tetrahedron 2009, 65, 4384
12. Reiehart, K. L.; Fregau, N. L.; Warwick, R. A.; Garcia Gravalos, D.; Avila, J.; Faircloth, G. T. PCT WO9952521 A1 19991021, 1999.
13. Sanchez, A. M.; Malagarie-Cazenave, S.; Olea, N.; Vara, D.; Cuevas, C.; Diaz-Laviada, I. Eur. J. Pharmacol. 2008, 584, 237
14. Williams, R. Expert Opin. Invest. Drugs 2009, 18, 1581
15. Garrido, L.; Zubia, E.; Ortega, M. J.; Naranjo, S.; Salva, J. Tetrahedron 2001, 57, 4579
16. Jares-Erijman, E. A.; Bapat, C. P.; Lithgow-Bertelloni, A.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 5732
17. Jimenez, C.; Crews, P. J. Nat. Prod. 1990, 53, 978
18. Kokotos, G.; Padrón, J. M.; Noula, C.; Gibbons, W. A.; Martín, V. S. Tetrahedron: Asymmetry 1996, 7, 857
19. Padrón, J. M.; Kokotos, G.; Martín, T.; Markidis, T.; Gibbons, W. A.; Martín, V. S. Tetrahedron: Asymmetry 1998, 9, 3381
20. Kokotos, G.; Padrón, J. M.; Martín, T.; Gibbons, W. A.; Martín, V. S. J. Org. Chem. 1998, 63, 3741
21. Padrón, J. M.; Martín, V. S.; Hadjipavlou-Litina, D.; Noula, C.; Constantinou-Kokotou, V.; Peters, G. J.; Kokotos, G. Bioorg. Med. Chem. Lett. 1999, 9, 821
22. Markidis, T.; Padrón, J. M.; Martín, V. S.; Peters, G. J.; Kokotos, G. Anticancer Res. 2001, 21, 2835
23. Padrón, J. M.; Peters, G. J. Invest. New Drugs 2006, 24, 195
24. Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. 1987, 26, 1141
25. Reetz, M. T.; Rölfing, K.; Griebenow, N. Tetrahedron Lett. 1994, 35, 1969
26. Reetz, M. T. Chem. Rev. 1999, 99, 1121
27. Bolis, G.; Fung, A. K.; Greer, J.; Kleinert, H. D.; Marcotte, P. A.; Perun, T. J.; Plattner, J. J.; Stein, H. H. J. Med. Chem. 1987, 30, 1729
28. Kano, S.; Yusa, Y.; Yokomatsu, T.; Shibuya, S. Chem. Pharm. Bull. 1989, 37, 2867
29. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N. J. Org. Chem. 1991, 56, 4370
30. Bonar-Law, R. P.; Davis, A. P.; Dorgan, B. J.; Reetz, M. T.; Wehrsig, A. Tetrahedron Lett. 1990, 31, 6725
31. Andrés, J. M.; Barrio, R.; Martínez, M. A.; Pedrosa, R.; Pérez-Encabo, A. J. Org. Chem. 1996, 61, 4210
32. Concellón, J. M.; Bernad, P. L.; Pérez-Andres, J. A. J. Org. Chem. 1997, 62, 8902
33. Oppolzer, W.; Tamura, O.; Sundarababu, G.; Singer, M. J. Am. Chem. Soc. 1992, 114, 5900
34. Andrés, J. M.; Muñoz, E. M.; Pedrosa, R.; Pérez-Encabo, A. Eur. J. Org. Chem. 2003, 3387
35. Andrés, J. M.; Pedrosa, R.; Pérez-Encabo, A. Eur. J. Org. Chem. 2006, 3442
36. Masuda, Y.; Tashiro, T.; Mori, K. Tetrahedron: Asymmetry 2006, 17, 3380
37. Andrés, J. M.; Pedrosa, R.; Pérez-Encabo, A. Tetrahedron Lett. 2006, 47, 5317
38. Andrés, J. M.; Pedrosa, R.; Pérez-Encabo, A.; Ramírez, M. Tetrahedron 2006, 62, 7783
39. Reetz, M. T.; Drewes, M. W.; Schwickardi, R. Org. Synth. 1999, 76, 110
40. Ordóñez, M.; de la Cruz, R.; Fernandez-Zertuche, M.; Muñoz-Hernández, M.-A. Tetrahedron: Asymmetry 2002, 13, 559
41. Polt, R.; Peterson, M. A.; De Yung, L. J. Org. Chem. 1992, 57, 5469
42. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199
43. Brook, M. A.; Chan, T. H. Synthesis 1983, 201
44. Mei, D.; Zhang, W.; Li, Y. Synth. Commun. 2010, 40, 1099
45. Higgins, G.; Slassi, A.; Isaac, M. US2010/0016403.
46. Andrés, J. M.; Pedrosa, R. Tetrahedron: Asymmetry 1998, 9, 2493
47. Laïb, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709
48. Bi-Shuang, C.; Long-He, Y.; Jian-Liang, Y.; Tao, H.; Yuan-Ping, R.; Jin, F.; Pei-Qiang, H. Eur. J. Med. Chem. 2011, 46, 5480
49. Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986, 51, 5320
50. Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321
51. Van Overmeire, I.; Boldin, S. A.; Dumont, F.; Van Calenbergh, S.; Slegers, G.; De Keukeleire, D.; Futerman, A. H.; Herdewijn, P. J. Med. Chem. 1999, 42, 2697
52. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511
53. Marshall, J. A.; Seletsky, B. M.; Coant, P. S. J. Org. Chem. 1994, 59, 5139
54. White, J. D.; Hansen, J. D. J. Org. Chem. 2005, 70, 1963
55. Hauser, F. M.; Rhee, R. P.; Ellenberger, S. R. J. Org. Chem. 1984, 49, 2236
56. Davies, S. G.; Smyth, G. D.; Chippindale, A. M. J. Chem. Soc., Perkin Trans. 1 1999, 3089
57. Ghosal, P.; Shaw, A. K. Tetrahedron Lett. 2010, 51, 4140
58. Xu, K.; Lai, G.; Zha, Z.; Pan, S.; Chen, H.; Wang, Z. Chem.-Eur. J. 2012, 18, 12357
59. Kobayashi, S.; Furuta, T. Tetrahedron 1998, 54, 10275