Biocatalytic asymmetric reduction of 3-acetylisoxazoles

Tetrahedron Asymmetry

Volumn 16, Issue 7, 2005, Pages 1403-1408

  Itoh, Ken Ichi ^a   Sakamaki, Hiroshi ^a   Nakamura, Kaoru ^b   Horiuchi, C Akira ^c  

^a NIHON UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c RIKKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACETYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 BROMOMETHYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 BUTYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 CHLOROMETHYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 HEXYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 PENTYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 PHENYLISOXAZOLE; 3(1 HYDROXYETHYL) 5 PROPYLISOXAZOLE; ISOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CARAGANA; CHEMICAL ANALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; REDUCTION; SYNECHOCOCCUS ELONGATUS; SYNECHOCYSTIS;

EID: 27644485521     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.02.024     Document Type: Article

References (28)

1. Lee, S. Y.; Lee, B. S.; Lee, C.-W.; Oh, D. Y. J. Org. Chem. 2000, 65, 256-257.
2. Kozikowski, A. P.; Adamczyk, M. Tetrahedron Lett. 1982, 23, 3123-3126.
3. Kozikowski, A. P.; Chen, Y. Y. J. Org. Chem. 1981, 46, 5248-5250.
4. Ko, D.-H.; Maponya, M. F.; Khalil, M. A.; Oriaku, E. T.; You, Z. Med. Chem. Res. 1997, 7, 313-323.
5. Kang, Y. Y.; Shin, K. J.; Yoo, K. H.; Seo, K. J.; Hong, C. Y.; Lee, C.-S.; Park, S. Y.; Kim, D. J.; Park, S. W. Bioorg. Med. Chem. Lett. 2000, 10, 95-99.
6. Conti, P.; Dallanoce, C.; Amici, M. D.; Micheli, C. D.; Klotz, K.-N. Bioorg. Med. Chem. 1998, 6, 401-408.
7. (a) Itoh, K.; Takahashi, S.; Ueki, T.; Sugiyama, T.; Takahashi, T. T.; Horiuchi, C. A. Tetrahedron Lett. 2002, 43, 7035-7037;
8. (b) Itoh, K.; Horiuchi, C. A. Tetrahedron 2004, 60, 1671-1681.
9. Enzyme Catalysis in Organic Synthesis A Comprehensive Handbook; Drauz, K., Waldmann, H., Eds.; Wiley-VCH: Weinheim, 2002.
10. Thujopsene; (a) Sakamaki, H.; Kitanaka, S.; Chai, W.; Hayashida, Y.; Takagi, Y.; Horiuchi, C. A. J. Nat. Prod. 2001, 64, 630-631;
11. (b) Chai, W.; Hayashida, Y.; Sakamaki, H.; Horiuchi, C. A. J. Mol. Catal. B: Enzym. 2004, 27, 55-60.
12. Ionone; Sakamaki, H.; Itoh, K.; Chai, W.; Hayashida, Y.; Kitanka, S.; Horiuchi, C. A. J. Mol. Catal. B: Enzym. 2004, 27, 177-181.
13. Matsuura, Y.; Chai, W.; Endoh, E.; Suhara, J.; Hamada, H.; Horiuchi, C. A. Phytochemistry 2002, 61, 669-673.
14. (a) Nakamura, K.; Yanamaka, R.; Tohi, K.; Hamada, H. Tetrahedron Lett. 2000, 41, 6799-6802;
15. (b) Nakamura, K.; Yamanaka, R. J. Chem. Soc., Chem. Commun. 2002, 16, 1782-1783;
16. (c) Nakamura, K.; Yamanaka, R. Tetrahedron: Asymmetry 2002, 13, 2529-2533.
17. Utsukihara, T.; Chai, W.; Kato, N.; Nakamura, K.; Horiuchi, C. A. J. Mol. Catal. B: Enzym. 2004, 31, 19-24.
18. Chai, W.; Sakamaki, H.; Kitanaka, S.; Horiuchi, C. A. Bull. Chem. Soc. Jpn. 2003, 76, 177-182.
19. (a) Nakamura, K.; Yamanaka, R. Tetrahedron: Asymmetry 2003, 14, 2659-2681;
20. (b) Nakamura, K.; Matsuda, T. In Enzyme Catalysis in Organic Synthesis A Comprehensive Handbook; Drauz, K., Waldmann, H., Eds.; Wiley-VCH: Weinheim, 2002, pp 991-1047.
21. Bajiley, D.; O'Hangan, D.; Dyer, U.; Lamont, R. B. Tetrahedron: Asymmetry 1993, 4, 1255-1258.
22. Ticozzi, C.; Zanarotti, A. Tetrahedron Lett. 1988, 29, 6167-6170.
23. Kawano, S.; Horikawa, N.; Yasohara, Y.; Hasegawa, J. Biosci. Biotech. Biochem. 2003, 67, 809-814.
24. Matsuda, T.; Harada, T.; Nakajima, N.; Itoh, T.; Nakamura, K. J. Org. Chem. 2000, 65, 157-163.
25. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
26. Nakamura, K.; Takenaka, K. Tetarehedron: Asymmetry 2002, 13, 415-422.
27. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519;
28. (b) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Boldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 57, 2370-2374.