Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

Tetrahedron Asymmetry

Volumn 15, Issue 24, 2004, Pages 3939-3944

  Kamal, Ahmed ^a   Shaik, Ahmad Ali ^a   Sandbhor, Mahendra ^a   Malik, M Shaheer ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AEGELINE; AZIDE; DENOPAMINE; HYDROXYAMIDE; TEMBAMIDE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA CEPACIA; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME KINETICS; ENZYME MECHANISM; NONHUMAN; PRIORITY JOURNAL; REDUCTION KINETICS;

EID: 9944226680     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.013     Document Type: Article

References (33)

1. For reviews, see: W. McCoull, and F.A. Davis Synthesis 2000 1347
2. H.M.L. Osborn, and J. Sweeney Tetrahedron: Asymmetry 8 1997 1693
3. D. Tanner Angew. Chem., Int. Ed. Engl. 33 1994 599
4. For reviews, see: S.C. Bergmeier Tetrahedron 56 2000 2561
5. D.J. Ager, I. Prakash, and D.R. Schaad Chem. Rev. 96 1996 835
6. J.R. Powell, I.W. Waimer, and D.E. Drayer Drug Stereochemistry Analytical Methods and Pharmacology 1998 Marcel Dekker New York
7. For a review see: R. Noyori, S. Suga, K. Kawai, S. Okada, M. Kitamura, N. Oguni, M. Hayashi, T. Kaneko, and Y. Matsuda J. Organomet. Chem. 382 1990 19 37
8. J. Elks, and C.R. Ganellin Dictionary of Drugs, Chemical Data, Structure and Bibliographies first ed. 1990 University Press Cambridge, GB p 358
9. A.M. Kuck, S.M. Albonico, and V. Deulofeu Chem. Ind. 1996 945 946
10. A. Chatterjee, and S. Bose J. Ind. Chem. Soc. 29 1952 425
11. S.R. Johns, J.A. Lamberton, and J.R. Price Aust. J. Chem. 20 1967 2795 2797
12. S.R. Johns, J.A. Lamberton, H.J. Tweeddale, and R.I. Willing Aust. J. Chem. 22 1969 2233 2236
13. R.F.C. Brown, W.R. Jackson, and T.D. McCarthy Tetrahedron: Asymmetry 4 1993 205 206
14. R.F.C. Brown, A.C. Donohue, W.R. Jackson, and T.D. McCarthy Tetrahedron 50 1994 13739 13752
15. A.M. Kuck, S.M. Albonico, and V. Deulofeu J. Chem. Soc., Sect. C 1967 1327 1328
16. T. Kappe, and M.D. Armstrong J. Med. Chem. 7 1964 569 571
17. O. Pamies, and J.E. Backvall J. Org. Chem. 66 2001 4022 4025
18. E. Foelsche, A. Hickel, H. Honig, and P. Seufer-Wasserthal J. Org. Chem. 55 1990 1749 1753
19. J.S. Yadav, P.T. Reddy, S. Nanda, and A.B. Rao Tetrahedron: Asymmetry 12 2001 3381 3385
20. B.T. Cho, S.K. Kang, and S.H. Shin Tetrahedron: Asymmetry 13 2002 1209 1217
21. A. Kamal, M. Sandbhor, and K.V. Ramana Tetrahedron: Asymmetry 13 2002 815
22. A. Kamal, M. Sandbhor, A.A. Shaik, and V. Sravanthi Tetrahedron: Asymmetry 14 2003 2839
23. A. Kamal, M. Sandbhor, and A.A. Shaik Tetrahedron: Asymmetry 14 2003 1575
24. A. Kamal, M. Sandbhor, K. Ahmad, S.F. Adil, and A.A. Shaik Tetrahedron: Asymmetry 14 2003 3861
25. A. Kamal, A.A. Shaik, M. Sandbhor, and M.S. Malik Tetrahedron: Asymmetry 15 2004 935 938
26. K. Naito, T. Nagao, M. Otsuka, S. Harigaya, and H. Nakajima Jpn. J. Pharmacol. 38 1985 235
27. K. Naito, K. Nagao, Y. Ono, M. Otsuka, S. Harigaya, and H. Nakajima Jpn. J. Pharmacol. 39 1985 541
28. T. Ikeo, T. Nagao, T. Suzuki, and H. Yabana Jpn. J. Pharmacol. 39 1985 191
29. G. Xin-Jian, L. Zu-Yi, and L. Guo-Qiang Tetrahedron 49 1993 5805 5816
30. J. Goswami, R.L. Bezbaruah, A. Goswami, and N. Borthakur Tetrahedron: Asymmetry 12 2001 3343 3348
31. R.F.C. Brown, W.R. Jackson, and T.D. McCarthy Tetrahedron: Asymmetry 4 1993 2149 2150
32. E.J. Corey, and J.O. Link J. Org. Chem. 56 1991 442 447
33. 3N (0.48 mL, 3.5 mmol) in dry THF (15 mL)