Enzymatic desymmetrization of 1,1′-methylenedi[(1R,1′S,3R, 3′S,5S,5′R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-ene-1-yl]: Novel precursors of long chain polyketides

Tetrahedron Asymmetry

Volumn 16, Issue 13, 2005, Pages 2277-2283

  Coste, Gérald ^a   Gerber Lemaire, Sandrine ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CARBENE; ESTER; FURAN DERIVATIVE; POLYKETIDE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; ENZYME DEGRADATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION KINETICS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANSESTERIFICATION;

EID: 22044431904     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.05.038     Document Type: Article

References (58)

1. S. Omura, and H. Tanaka Macrolide Antibiotics: Chemistry, Biology and Practise 1984 Academic Press New York
2. S.D. Rychnovsky, G. Griesgraber, and R. Schlegel J. Am. Chem. Soc. 117 1995 197 210
3. T.I. Richardson, and S.D. Rychnovsky J. Org. Chem. 61 1996 4219 4231
4. B.H. Lipschutz, B. Ullman, C. Lindsley, S. Recchi, D.J. Buzard, and D. Dickson J. Org. Chem. 63 1998 6092 6093
5. J. Pawlak, P.P. Sowinski, E. Borowski, and P. Garibaldi J. Antibiot. 48 1995 1034 1038
6. G.J. McGarvey, J.A. Mathys, K.J. Wilson, K.O. Overly, P.T. Buonova, and P.G. Spours J. Am. Chem. Soc. 60 1995 7778 7790
7. T. Mukhopadhyay, E.K.S. Vijayakumar, S.R. Nadkarni, H.W. Fehlhaber, H. Kogler, and S. Petry J. Antibiot. 57 1998 582 585
8. For recent papers, see, for example: G.J. McGarvey, J.A. Mathys, and K.J. Wilson Tetrahedron Lett. 41 2000 6011 6015
9. P.B. Greer, and W.A. Donaldson Tetrahedron Lett. 41 2000 3801 3803
10. P.A. Wender, and B. Lippa Tetrahedron Lett. 41 2000 1007 1011
11. J. Kiegiel, J. Józwik, K. Wozniak, and J. Jurczak Tetrahedron Lett. 41 2000 4959 4963
12. A.G.M. Barrett, D.C. Braddock, P.D. de Koning, A.J.P. White, and D.J. Williams J. Org. Chem. 65 2000 375 380
13. S.T. Sarraf, and J.L. Leighton Org. Lett. 2 2000 1209 1212
14. M.J. Zacuto, and J.L. Leighton J. Am. Chem. Soc. 122 2000 8587 8688
15. S.I. Kiyoota, M.A. Hena, T. Yabukami, K. Murai, and F. Goto Tetrahedron Lett. 41 2000 7511 7516
16. S. Bouzbouz, and J. Cossy Org. Lett. 2 2000 3975 3977
17. Org. Lett. 2 2000 501 504
18. T. Trieselmann, and R.W. Hoffmann Org. Lett. 2 2000 1209 1212
19. I. Paterson, and L.A. Collett Tetrahedron Lett. 42 2001 1187 1191
20. T.J. Hunter, and G.A. O'Doherty Org. Lett. 3 2001 1049 1052
21. C.J. Sinz, and S.D. Rychnovsky Angew. Chem., Int. Ed. 40 2001 3224 3227
22. D.J. Kopecky, and S.D. Rychnovsky J. Am. Chem. Soc. 123 2001 8420 8421
23. S.A. Burova, and F.E. McDonald J. Am. Chem. Soc. 124 2002 8188 8189
24. C. Schneider, F. Tolksdorf, and M. Rehfeuter Synlett 2002 2098 2100
25. J.N. Sheperd, and D.C. Myles Org. Lett. 2003 1027 1030
26. I. Paterson, and G.J. Florence Eur. J. Org. Chem. 2003 2193 2208
27. M.J. Zacuto, S.J. O'Malley, and J.L. Leighton Tetrahedron 59 2003 8889 8900
28. M.C. Della, N. Maulucci, F. De Riccardis, and I. Izzo Tetrahedron: Asymmetry 14 2003 3371 3378
29. A.B. Smith III, S.M. Pitram, A.M. Boldi, M.J. Gaunt, C. Sfouggatakis, and W.H. Moser J. Am. Chem. Soc. 125 2005 14435 14445
30. M. Turks, F. Fonquerne, and P. Vogel Org. Lett. 6 2004 1053 1056
31. L.D. Fader, and E.M. Carreira Org. Lett. 6 2004 2485 2488
32. L.A. Wessjohann, H. Wild, and H.S. Schrekker Tetrahedron Lett. 45 2004 9073 9078
33. I. Paterson, O. Delgado, G.J. Florence, I. Lyothier, M. O'Brien, J.P. Scott, and N. Sereinig J. Org. Chem. 70 2005 150 160
34. A.B. Smith III, S.P. Walsh, M. Frohn, and M.O. Duffey Org. Lett. 7 2005 139 142
35. P. Vogel, S. Gerber-Lemaire, A.T. Carmona, K.T. Meilert, and M.E. Schwenter Pure Appl. Chem. 77 2005 131 137
36. J. De Vicente, B. Betzemeier, and S.D. Rychnovsky Org. Lett. 7 2005 1853 1856
37. N. Lohse-Fraefel, and E.M. Carreira Org. Lett. 7 2005 2011 2014
38. K.M. Meilert, M.E. Schwenter, Y. Shatz, S.R. Dubbaka, and P. Vogel J. Org. Chem. 68 2003 2964
39. M.E. Schwenter, and P. Vogel Chem. Eur. J. 6 2000 4091 4103
40. M.E. Schwenter, and P. Vogel J. Org. Chem. 66 2001 7869 7872
41. A.G. Csákÿ, and P. Vogel Tetrahedron: Asymmetry 11 2000 4935 4944
42. S. Gerber-Lemaire, and P. Vogel Eur. J. Org. Chem. 2003 2959 2963
43. S. Gerber-Lemaire, and P. Vogel Eur. J. Org. Chem. 2004 5040 5046
44. For recent papers on desymmetrization, see: E. GarcIÍa-Urdiales, I. Alfonso, and V. Gotor Chem. Rev. 105 2005 313 354 and references cited therein
45. K. Hegemann, R. Fröhlich, and G. Haufe Eur. J. Org. Chem. 2004 2181 2192
46. B.M. Trost, and T. Mino J. Am. Chem. Soc. 125 2003 2410 2411
47. C. Marchionni, and P. Vogel Helv. Chim. Acta 84 2001 431 472
48. C. Marchionni, K. Meilert, P. Vogel, and K. Schenk Synlett 2000 1111 1114
49. P. Vogel Curr. Org. Chem. 2 1998 255 280
50. Z. Dienes, and P. Vogel J. Org. Chem. 61 1996 6958 6970
51. J. Ancerewicz, P. Vogel, and K. Schenk Helv. Chim. Acta 79 1996 1415 1427
52. J. Ancerewicz, and P. Vogel Helv. Chim. Acta 79 1996 1393 1414
53. C. Marchionni, P. Vogel, and P. Roversi Tetrahedron Lett. 37 1996 4149 4152
54. Z. Dienes, and P. Vogel Bioorg. Med. Chem. Lett. 5 1995 547 550
55. Z. Dienes, T. Antonsson, and P. Vogel Tetrahedron Lett. 34 1993 1013 1016
56. T. Antonsson, and P. Vogel Tetrahedron Lett. 31 1990 89 92
57. N. Harada, and K. Nakanishi Circular Dichroic Spectroscopy Exciton Coupling in Organic Chemistry 1983 University Science Books Hill Valley, CA
58. Crystallographic data (excluding structure factors) for the structure herein have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 270615. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK.