Chemoenzymatic synthesis of (R)-(+)-α-(4-fluorophenyl)-4-(2-pyrimidinyl)-1-piperazinebutanol and (R)-(+)-α-(4-fluorophenyl)-4-methyl-1-piperidinebutanol as potential antipsychotic agents

Tetrahedron

Volumn 53, Issue 44, 1997, Pages 15115-15122

  Gil, Nicolás ^a   Bosch, Ma Pilar ^a   Guerrero, Angel ^a  

^a DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA (4 FLUOROPHENYL) 4 (5 FLUORO 2 PYRIMIDINYL) 1 PIPERAZINEBUTANOL; NEUROLEPTIC AGENT;

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

EID: 0030804404     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10009-6     Document Type: Article

References (21)

1. Creese, I.; Burt, D. R.; Snyder, S. H. Science 1976, 192, 481.
2. Seeman, P. Biochem. Pharmacol. 1977, 26, 1741.
3. Bjerkenstedt, L.; Eneroth, P.; Härnryd, C.; Sedvall, G. Arch. Psychiatr. Nervenkr. 1977, 224, 281.
4. Wiesel, F.-A.; Bjerkenstedt, L.; Skett, P. Acta Pharmacol. Toxicol. 1978, 43, 129.
5. Yevich, J. P.; New, J. S.; Lobeck, W. G.; Dextraze, P.; Bernstein, E.; Taylor, D. P.; Yocca, F. D.; Eison, M. S.; Temple, J., D.L. J. Med. Chem. 1992, 35, 4516.
6. Chen, C. S.; Sih, C. J. Angew. Chem. Int. Ed. Engl. 1989, 28, 695.
7. Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Heidelberg, 1992.
8. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
9. Poppe, L.; Novák, L. Selective Biocatalysis; CVCH: Weinheim, 1992.
10. Theil, F. Chem. Rev. 1995, 95, 2203.
11. Ramachandran, P. V.; Gong, B.; Brown, H. C. Tetrahedron: Asymmetry 1993, 4, 2399.
12. Gaspar, J.; Guerrero, A. Tetrahedron: Asymmetry 1995, 6, 231.
13. Petschen, I.; Malo, E. A.; Bosch, M. P.; Guerrero, A. Tetrahedron: Asymmetry 1996, 7, 2135.
14. Bianchi, D.; Moraschini, P.; Bosetti, A.; Cesti, P. Tetrahedron: Asymmetry 1994, 5, 1917.
15. Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem. 1988, 53, 5531-5534.
16. Nakamura, K.; Kinoshita, M.; Ohno, A. Tetrahedron 1994, 50, 4681.
17. Dale, D. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
18. 4 reduction (see ref 5).
19. Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
20. Kaslauskas, R.J.; Weissfloch, A.N.E.; Rappaport, A.T.; Cuccia, L.A. J. Org. Chem. 1991, 56, 2656.
21. Theil, F.; Lemke, K.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron: Asymmetry 1995, 6, 1323.