Asymmetric synthesis of both the enantiomers of antidepressant venlafaxine and its analogues

Tetrahedron Letters

Volumn 53, Issue 15, 2012, Pages 1990-1992

  Bhuniya, Rajib ^a   Nanda, Samik ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Antidepressants; Asymmetric synthesis; Hydroxynitrile lyase; Lipase catalyzed kinetic resolution

Indexed keywords

CYANOHYDRIN; HYDROXYNITRILE LYASE; KETONE; TRIACYLGLYCEROL LIPASE; VENLAFAXINE;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; ENANTIOMER; KINETICS; STEREOCHEMISTRY;

HEVEA BRASILIENSIS;

EID: 84858151784     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.025     Document Type: Article

References (27)

1. Mahaney, P. E.; Trybulski, E. J.; Gavrin, L. K.; Vu, A. T. US 7531543 B2 20090512.
2. Mahaney, P. E. US 7524846 B2 20090428.
3. Trybulski, E. J.; Mahaney, P. E.; Gavrin, L. K.; Moore, W. J.; Sabatucci, J. P. US 7491723 B2 20090217.
4. Trybulski, E. J.; Sabatucci, J. P.; Vu, A. T.; Cohn, S. T.; Santilli, A. A.; Gavrin, L. K.; Ye, F.; Mahaney, P. E. WO 2005037809 A1 20050428.
5. Mahaney, P. E.; Antane, M. M.; Sun, J. S. WO 2007067501 A1 20070614.
6. Nanaji, T. S.; Mathurbhai, P. H.; Sadanand, N. S. IN 2004KO00215 A 20070330.
7. Rameshchandra, S. B.; Patel, M. S.; Patel, G. B.; Ramakrishna, N. V. S.; Manakiwala, S. C.; Agarwal, V. K.; Pandita, K.; Patel, P. R. WO 2003050074 A1 20030619.
8. M. Panunzio, E. Bandini, A. D'Aurizio, Z. Xia, and X. Mu Synthesis 2008 1753 1756
9. K.A. Kochetkov, M.A. Galkina, and O.M. Galkin Mendeleev Commun. 20 2010 314 315
10. M. Avi, M.H. Fechter, K. Gruber, F. Belaj, P. Pochlauer, and H. Griengl Tetrahedron 60 2004 10411 10418
11. R. Bhunya, N. Jana, T. Das, and S. Nanda Synlett 2009 1237 1240
12. R. Bhunya, T. Mahapatra, and S. Nanda Tetrahedron: Asymmetry 20 2009 1526 1530
13. M. Brovetto, D. Gamenara, P.S. Mendez, and G.A. Seoane Chem. Rev. 111 2011 4346 4403
14. M. Piotrowski Phytochemistry 69 2008 2655 2667
15. J. Holt, and U. Hanefeld Curr. Org. Synth. 6 2009 15 37
16. R. Kourist, P. Dominiguez de Maria, and U.T. Bornscheuer ChemBioChem 9 2008 491 498
17. T. Purkarthofer, W. Skranc, C. Schuster, and H. Griengl Appl. Microbiol. Biotechnol. 76 2007 309 320
18. C. Kobler, A. Bohrer, and F. Effenberger Tetrahedron 60 2004 10397 10410
19. F. Effenberger, J. Roos, and C. Kobler Angew. Chem., Int. Ed. 41 2000 1876 1879
20. F. Effenberger, J. Roos, C. Kobler, and H. Buhler Can. J. Chem. 80 2002 671 679
21. K. Smith, and A. Pelter B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 8 1991 Pergamon Press Oxford 703 731
22. M. Zaidlewicz, and A. Pelter G. Helmche, R.W. Hoffmann, J. Mulzer, E. Schaumann, Stereoselective Synthesis Vol. E21 7 1991 Houben-Weyl, Georg Thieme Stuttgart 4396 4420 fourth ed.
23. E.M. Carreira, and L. Kvaerno Classics in Stereoselective Synthesis 2009 Wiley-VCH pp. 215-232
24. H.C. Brown, P.K. Jadhav, and A.K. Mandal Tetrahedron 37 1981 3547 3587
25. A.N.E. Weissfloch, and R.J. Kazlauskas J. Org. Chem. 60 1995 6959 6969
26. B. Bonnaud, H. Cousse, G. Mouzin, M. Briley, A. Stenger, F. Fauran, and J.P. Couzinier J. Med. Chem. 30 1987 318 325
27. J.P. Yardley, J.G.E. Morris Husbands, G. Stack, J. Butch, J. Bicksler, J.A. Moyer, E.A. Muth, T. Andree, H. Fletcher, M.N.G. James, and A.R. Sieleckit J. Med. Chem. 33 1990 2899 2905 Literature [ α ] D 25 for (S)-venlafaxine = +27.6 (c = 1.07, EtOH); for (R)-venlafaxine [ α ] D 25 -27.1 (c = 1.04, EtOH).