Asymmetric reduction of 3-aryl-3-keto esters using Rhizopus species

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 14, 2006, Pages 4918-4922

  Salvi, Neeta A ^a   Chattopadhyay, Subrata ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

Keto esters; Biotransformation; Enantioselective; Microbial reduction

Indexed keywords

2 FLUOROPHENYL; 3 ARYL 3 KETO ESTER DERIVATIVE; 3 NITROPHENYL; 4 NITROPHENYL; BENZENE DERIVATIVE; DIPHENYL ETHER DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DECARBOXYLATION; ENANTIOSELECTIVITY; HYDROLYSIS; INCUBATION TIME; NONHUMAN; REDUCTION; RHIZOPUS;

ALCOHOLS; BIOTRANSFORMATION; ESTERS; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PROPIONATES; RHIZOPUS; STEREOISOMERISM;

FUNGI; RHIZOPUS; RHIZOPUS ORYZAE;

EID: 33646810423     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.03.025     Document Type: Article

References (46)

1. Thaisrivongs S., Pals D.T., Kati W.M., Turner S.R., Thomasco L.M., and Watt W. J. Med. Chem. 29 (1986) 2080-2087
2. Thaisrivongs S., Schostarez H.J., Pals D.T., Kati W.M., and Turner S.R. J. Med. Chem. 30 (1987) 1837-1842
3. Schostarez H.J. J. Org. Chem. 53 (1988) 3628-3631
4. Oertle K., Beyeler H., Duthaler R.O., Lottenbach W., Riediker M., and Steiner E. Helv. Chim. Acta 73 (1990) 353-358
5. Masamune S., Choy W., Petersen J.S., and Sita L.R. Angew. Chem., Int. Ed. Engl. 24 (1985) 1-30
6. Nicolaou K.C., Chakraborty T.K., Ogawa Y., and Furst G.T. J. Am. Chem. Soc. 110 (1988) 4660-4672
7. Tatsuta K., Amemiya Y., Kanemura Y., Takahashi H., and Kinoshita M. Tetrahedron Lett. 23 (1982) 3375-3378
8. Schlessinger R.H., Poss M.A., and Richardson S. J. Am. Chem. Soc. 108 (1986) 3112-3114
9. Narasaka K., and Pai F.-C. Tetrahedron 40 (1984) 2233-2238
10. Evans D.A., Chapman K.T., and Carreira M.E. J. Am. Chem. Soc. 110 (1988) 3560-3578
11. Haddad M., Dorbais J., and Larcheveque M. Tetrahedron Lett. 38 (1997) 5981-5984
12. Narasaka K., Ukaji Y., and Yamazaki S. Bull. Chem. Soc. Jpn. 59 (1986) 525
13. Wang Y.-F., Izawa T., Kobayashi S., and Ohno M. J. Am. Chem. Soc. 104 (1982) 6465-6466
14. Hashiguchi S., Kawada A., and Natsugari H. J. Chem. Soc. Perkin Trans. 1 (1991) 2435-2444
15. Hayashi Y., Rode J.J., and Corey E.J. J. Am. Chem. Soc. 118 (1996) 5502-5503
16. Senanayake C.H., Fang K., Grover P., Bakale R.P., Vandenbossche C.P., and Wald S.A. Tetrahedron Lett. 40 (1999) 819-822
17. Genov M., Dimitrov V., and Ivanova V. Tetrahedron Asymm. 8 (1997) 3703-3706
18. Eliel E.L., and He X.-C. J. Org. Chem. 55 (1990) 2114-2119
19. Foster B.J., and Lavagnino E.R. Drugs of the Future Vol. 11 (1986), Prous Science, Barcelona, Spain 134-200
20. Robertson D.W., Krushins J.H., Fuller R.W., and Leander J.D. J. Med. Chem. 31 (1988) 1412-1417 and references therein
21. Mochizuki N., Sugai T., and Ohta H. Biosci. Biotech. Biochem. 58 (1994) 1666-1670
22. Ankier S.I. Prog. Med. Chem. 23 (1986) 121-140
23. Duthaler R.O., Herold P., Lottenbach W., Oertle K., and Riediker M. Angew. Chem. Int. Ed. Engl. 28 (1989) 495-497
24. Mioskowski C., and Solladie G. Tetrahedron 36 (1979) 227-236
25. Meyers A.I., and Knaus G. Tetrahedron Lett. 15 (1974) 1333-1336
26. Noyori R. Asymmetric Catalysis in Organic Chemistry (1994), Wiley & Sons, New York p. 62
27. Ireland T., Grossheimann G., Wieser J.C., and Knochel P. Angew. Chem. Int. Ed. 38 (1999) 3212-3214
28. Ratovelomanana V.V., and Genet J.P. J. Organomet. Chem. 567 (1998) 163-171
29. Everaere K., Carpentier J.F., Mortreux A., and Bulliard M. Tetrahedron: Asymmetry 10 (1999) 4663-4666
30. Sun Y., Wan X., Guo M., Wang D., Dong X., Plan Y., and Zhang Z. Tetrahedron: Asymmetry 15 (2004) 2185-2188
31. For a comprehensive review of this area, see:. Davies H.G., Green R.H., Kelly D.R., and Roberts S.M. Biotransformations in Preparative Organic Chemistry. The Use of Isolated Enzymes and Whole Cell Systems in Synthesis (1989), Academic Press, London (Chapter 3)
32. Azerad R., and Buisson D. In: Servi S. (Ed). Microbial Reagents in Organic Synthesis (1992), Kluwer Academic Publishers, Dordecht, The Netherlands 421-440
33. Nakamura K., Fuji M., and Ida Y. Tetrahedron: Asymmetry 12 (2001) 3147-3153
34. Padhi S.K., and Chadha A. Tetrahedron: Asymmetry 16 (2005) 2790-2798
35. Sharma A., and Chattopadhyay S. J. Mol. Cat. B: Enzymatic 10 (2000) 531-534
36. Xu C., and Yaun C. Tetrahedron 61 (2005) 2169-2186
37. Salvi N.A., Patil P.N., Udupa S.R., and Banerji A. Tetrahedron: Asymmetry 6 (1995) 2287-2290
38. Salvi N.A., Udupa S.R., and Banerji A. Biotechnol. Lett. 20 (1998) 201-203
39. Salvi N.A., and Chattopadhyay S. Tetrahedron 57 (2002) 2833-2839
40. Salvi N.A., Badheka L.P., and Chattopadhyay S. Biotechnol. Lett. 25 (2003) 1081-1086
41. Salvi N.A., and Chattopadhyay S. Tetrahedron: Asymmetry 15 (2004) 3397-3400
42. Deol B.S., Ridly D.D., and Simpson G.W. Aust. J. Chem. 29 (1976) 2459-2467
43. Medson C., Smallridge A.J., and Ttewhella M.A. Tetrahedron: Asymmetry 8 (1997) 1049-1054
44. Dale J.A., and Mosher S.H. J. Am. Chem. Soc. 95 (1973) 512-519
45. Faber K., and Riva S. Synthesis (1992) 895-910
46. Santaniello E., Ferraboschi P., Grisenti P., and Manzocchi A. Chem. Rev 92 (1992) 1071-1140 and references cited therein