Synthesis and resolution of a key building block for epothilones: A comparison of asymmetric synthesis, chemical and enzymatic resolution

Tetrahedron Asymmetry

Volumn 15, Issue 18, 2004, Pages 2861-2869

  Scheid, Günther ^a   Ruijter, Eelco ^a   Konarzycka Bessler, Monika ^b   Bornscheuer, Uwe T ^b   Wessjohann, Ludger A ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EPOTHILONE DERIVATIVE; ESTERASE; KETONE DERIVATIVE; RECOMBINANT ENZYME; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA ANTARCTICA; CHEMICAL REACTION KINETICS; COMPARATIVE STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME CHEMISTRY; KINETICS; PRIORITY JOURNAL; STREPTOMYCES; SYNTHESIS; TECHNIQUE;

EID: 4644242591     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.06.048     Document Type: Article

References (39)

1. G.O. Scheid, W. Kuit, E. Ruijter, R.V.A. Orru, E. Henke, U. Bornscheuer, and L.A. Wessjohann Eur. J. Org. Chem. 2004 1063 1074
2. T. Gabriel, and L.A. Wessjohann Tetrahedron Lett 38 1997 1363 1366
3. T. Gabriel, and L.A. Wessjohann Tetrahedron Lett 38 1997 4387 4388
4. Scheid, G. O.; Eichelberger, U.; Wessjohann, L. A. Tetrahedron Lett. submitted for publication
5. Wessjohann, L. A.; Scheid, G. O. Deutsche Offenlegungsschrift DE0010051136A1 (18.04.2002), Germany, 16.10.2000, CA 136: 325358
6. Wessjohann, L. A.; Scheid, G. O.; Bornscheuer, U.; Henke, E.; Kuit, W.; Orru, R. V. A. Deutsche Offenlegungsschrift DE0010134172A1 (23.01.2003), Germany, 13.07.2001
7. Wessjohann, L. A.; Scheid, G. O.; Bornscheuer, U.; Henke, E.; Kuit, W.; Orru, R. V. A. Patent WO2002/032844A2 (25.04.2002), EP 200111992, International, 16.10.2001, CA 136:340534
8. K. Gerth, N. Bedorf, G. Höfle, H. Irschik, and H. Reichenbach J. Antibiotics 49 1996 560 564
9. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, and H. Reichenbach Angew. Chem., Int. Ed. 35 1996 1567 1569
10. Wessjohann, L. A.; Ruijter, E.; Garcia-Rivera, D.; Brandt, W. Mol. Div., in press
11. L. He, G.A. Orr, and S.B. Horwitz Drug Discov. Today 6 2001 1153 1164
12. E. Rudolf, and M. Červinka Curr. Med. Chem.-Anti-Cancer Agents 3 2003 421 429
13. D.M. Bollag, P.A. McQueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, and C.M. Woods Cancer Res. 55 1995 2325 2333
14. K.C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M.R.V. Finlay, and Y. Yang J. Am. Chem. Soc. 119 1997 7974 7991
15. A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E.J. Sorensen, and S. Danishefsky J. Angew. Chem. 108 1996 2976 2978
16. C.R. Harris, and S.J. Danishefsky J. Org. Chem. 64 1999 8434 8456
17. K.C. Nicolaou, F. Roschangar, and D. Vourloumis Angew. Chem., Int. Ed. 37 1998 2014 2045
18. J. Mulzer Monatsh. Chem. 131 2000 205 238
19. L.A. Wessjohann Angew. Chem. 109 1997 738 742
20. Angew. Chem., Int. Ed. 36 1997 715 718
21. L.A. Wessjohann, and G.O. Scheid H.-G. Schmalz Organic Synthesis Highlights Vol. 4 2000 Wiley-VCH Weinheim 251 267
22. K.-H. Altmann Curr. Opin. Chem. Biol. 5 2001 424 431
23. N. Bischofsberger, H. Waldmann, T. Saito, E.S. Simon, W. Lees, M.D. Bednarski, and G.M. Whitesides J. Org. Chem. 53 1988 3457 3465
24. W.J. Close J. Org. Chem. 15 1950 1131 1134
25. G. Cardillo, M. Orena, M. Romero, and S. Sandri Tetrahedron 45 1989 1501 1508
26. M.D. Chapell, S.J. Stachel, C.B. Lee, and S. Danishefsky J. Org. Lett. 2 2000 1633 1636
27. R. Noyori Asymmetric Catalysis in Organic Synthesis 1993 John Wiley & Sons New York
28. A. Musidlowska-Persson, and U.T. Bornscheuer Tetrahedron: Asymmetry 14 2003 1341 1344
29. A. Musidlowska, S. Lange, and U.T. Bornscheuer Angew. Chem., Int. Ed. 40 2001 2851 2853
30. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
31. N. Krebsfänger, F. Zocher, J. Altenbuchner, and U.T. Bornscheuer Enzyme Microb. Technol. 21 1998 641 646
32. V. Khalameyzer, I. Fischer, U.T. Bornscheuer, and J. Altenbuchner Appl. Environm. Microbiol. 65 1999 477 482
33. V. Khalameyzer, and U.T. Bornscheuer Biotechnol. Lett. 21 1999 101 104
34. M. Raban, and K. Mislow Tetrahedron Lett. 48 1965 4249 4253
35. S.K. Latypov, J.M. Seco, E. Quiñoá, and R. Riguera J. Am. Chem. Soc. 120 1998 877 882
36. For chemoenzymatic approaches to other epothilone fragments see: K. Shioji, H. Kawaoka, A. Miura, and K. Okuma Synth. Commun. 31 2001 3569 3575
37. B. Zhu, and J.S. Panek Tetrahedron Lett. 41 2000 1863 1866
38. T.D. Machajewski, and C.-H. Wong Synthesis 1999 1469 1472
39. U.T. Bornscheuer, J. Altenbuchner, and H.H. Meyer Biotechnol. Bioeng. 58 1998 554 559