Asymmetric synthesis of the C1-C13 fragment of the marine metabolite bistramide K

European Journal of Organic Chemistry

Volumn , Issue 32, 2010, Pages 6207-6216

  Bauder, Claude ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Asymmetric synthesis; Chiral auxiliary; Diastereoselectivity; Natural products; Olefination

Indexed keywords

EID: 78249243831     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000881     Document Type: Article

References (54)

1. J. P. Henichart, Y. Barbin, D. Laurent, J. F. Verbist, Tetrahedron 1988, 44, 451 - 459.
2. D. Gouiffes, M. Juge, N. Grimaud, L. Welin, M. P. Sauviat, Y. Barbin, D. Laurent, C. Roussakis, J. P. Henichart, J. F. Verbist, Toxicon 1988, 26, 1129 - 1136.
3. B. M. Degnan, C. J. Hawkins, M. F. Lavin, E. J. McCaffrey, D. L. Parry, D. J. Watters, J. Med. Chem. 1989, 32, 1354 - 1359.
4. J. F. Biard, C. Roussakis, J. M. Kornprobst, D. Gouiffes-Barbin, J. F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland, C. Debitus, J. Nat. Prod. 1994, 57, 1336-1345: Bistramides B, C, D, and K were first isolated in New Caledonia.
5. B. T. Murphy, S. Cao, P. Brodie, J. Maharavo, H. Andriamanantoanina, P. Ravelonandro, D. G. I. Kingston, J. Nat. Prod. 2009, 72, 1338 - 1340.
6. M. P. Foster, C. L. Mayne, R. Dunkel, R. J. Pugmire, D. M. Grant, J. M. Kornprobst, J. F. Verbist, J. F. Biard, C. M. Ireland, J. Am. Chem. Soc. 1992, 114, 1110 - 1111.
7. P. Wipf, Y. Uto, S. Yoshimura, Chem. Eur. J. 2002, 8, 1670 - 1681.
8. P. Wipf, T. D. Hopkins, Chem. Commun. 2005, 3421 - 3423.
9. G. Zuber, M.-R. Goldsmith, T. D. Hopkins, D. N. Beratan, P. Wipf, Org. Lett. 2005, 7, 5269 - 5272.
10. A. V. Statsuk, D. Liu, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 9546 - 9547.
11. M. T. Crimmins, A. C. DeBaillie, J. Am. Chem. Soc. 2006, 128, 4936 - 4937.
12. J. T. Lowe, I. E. Wrona, J. S. Panek, Org. Lett. 2007, 9, 327 - 330.
13. J. S. Yadav, L. Chetia, Org. Lett. 2007, 9, 4587 - 4589.
14. P. O. Gallagher, C. S. P. McErlean, M. F. Jacobs, D. J. Watters, W. Kitching, Tetrahedron Lett. 2002, 43, 531 - 535.
15. J. T. Lowe, J. S. Panek, Org. Lett. 2005, 7, 3231 - 3234.
16. R. W. Bates, K. Palani, Tetrahedron Lett. 2008, 49, 2832 - 2834.
17. M.-A. Hiebel, B. Pelotier, P. Goekjian, O. Piva, Eur. J. Org. Chem. 2008, 713 - 720.
18. M.-A. Hiebel, B. Pelotier, P. Lhoste, O. Piva, Synlett 2008, 1202 - 1204.
19. E. Gálvez, R. Parelló, P. Romea, F. Urpí, Synlett 2008, 2951 - 2954.
20. I. E. Wrona, J. T. Lowe, T. J. Turbyville, T. R. Johnson, J. Beignet, J. A. Beutler, J. S. Panek, J. Org. Chem. 2009, 74, 1897 - 1916.
21. G. Solladié, C. Bauder, J. F. Biard, Tetrahedron Lett. 2000, 41, 7747 - 7750.
22. S. A. Rizvi, V. Tereshko, A. A. Kossiakoff, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 3882 - 3883.
23. C. Bauder, J. F. Biard, G. Solladié, Org. Biomol. Chem. 2006, 4, 1860 - 1862.
24. G. Griffiths, B. Garrone, E. Deacon, P. Owen, J. Pongracz, G. Mead, A. Bradwell, D. Watters, L. Lord, Biochem. Biophys. Res. Commun. 1996, 222, 802 - 808.
25. A. V. Statsuk, R. Bai, J. L. Baryza, V. A. Verma, E. Hamel, P. A. Wender, S. A. Kozmin, Nat. Chem. Biol. 2005, 1, 383 - 388.
26. S. A. Rizvi, V. Tereshko, A. A. Kossiakoff, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 3882 - 3883.
27. S. A. Rizvi, D. S. Courson, V. A. Keller, R. S. Rock, S. A. Kozmin, Proc. Natl. Acad. Sci. USA 2008, 105, 4088 - 4092.
28. J. F. Biard, C. Roussakis, J. M. Kornprobst, D. Gouiffes-Barbin, J. F. Verbist, P. Cotelle, M. P. Foster, C. M. Ireland, C. Debitus, J. Nat. Prod. 1994, 57, 1336 - 1345.
29. J. Pusset, B. Maillere, C. Debitus, J. Nat. Toxins 1996, 5, 1 - 6.
30. H. L. Sings, K. L. Rinehart, J. Ind. Microbiol. 1996, 17, 385 - 396.
31. S. Siavoshian, C. Jacquot, J. F. Biard, G. Briand, C. Roussakis, Anticancer Res. 1999, 19, 5361 - 5365.
32. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127 - 2129.
33. Recently, this product was synthesized in a two-step procedure in 38% yield starting from (chloroacetyl)oxazolidinone. When we applied this method, we observed the formation of the diene product, probably due to elimination of the hydroxy group in the acidic medium:, S. J. B. Son, M.-H. Hwang, W. Lee, D.-H. Lee, Org. Lett. 2007, 9, 3897 - 3900.
34. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512 - 519.
35. J. R. Parikh, W. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505 - 5507.
36. 3)} as well as our analysis on the Mosher's ester derivative of compound 1 (the precursor of 3 and 4) verified the correct absolute stereochemistry and high optical purity for compounds 3 and 4:, E.-M. Moffatt, E. J. Thomas, Tetrahedron 1999, 55, 3723 -3734.
37. 3)}:, G. Pattenden, N. J. Ashweek, C. A. G. Baker-Glenn, J. Kempson, G. M. Walker, J. G. K. Yee, Org. Biomol. Chem. 2008, 6, 1478 - 1497.
38. Only the (E)-olefination product was detected. Spectral data for enone 8 are given in the Experimental Section.
39. The preparation of phosphonate 12 required the addition of HMPA. Indeed, the reaction did not exceed 5-10% without HMPA even at room temp. for 24 h.
40. 31P) of the crude material indicated that addition of phosphonate 12 to the aldehyde 4 did actually occur but without elimination to produce the olefination adduct.
41. M. Julia, J.-M. Paris, Tetrahedron Lett. 1973, 14, 4833 - 4836.
42. P. J. Kocienski, B. Lythgoe, S. Ruston, J. Chem. Soc. Perkin Trans. 1 1978, 829 - 834.
43. P. J. Kocienski, B. Lythgoe, S. Ruston, J. Chem. Soc. Perkin Trans. 1 1979, 1290 - 1293.
44. P. R. Blakemore, W. J. Cole, P. J. Kocienski, A. Morley, Synlett 1998, 26 - 28.
45. P. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563 - 2585.
46. C. Aäraquo;ssa, Eur. J. Org. Chem. 2009, 1831 - 1844.
47. A. R. Katritzky, J. M. Aurrecoechea, L. M. Vazquez de Miguel, J. Chem. Soc. Perkin Trans. 1 1987, 769 - 774.
48. H. S. Schultz, H. B. Freyermuth, S. R. Buc, J. Org. Chem. 1963, 28, 1140 - 1142.
49. 3Si], 15.9 (MeS), 14.1 (C-10), -4.3 (MeSi), -4.4 (MeSi) ppm.
50. 3 (1 g/5 mL in MeCN). The elution was performed with EtOAc/cyclohexane (5:95). For more details, see
51. C. M. Williams, L. N. Mander, Tetrahedron 2001, 57, 425 - 447.
52. T.-S. Li, J.-T. Li, H.-Z. Li, J. Chromatogr. A 1995, 715, 372 - 375.
53. H. Tian, X. Jiao, P. Xie, X. Liang, Tetrahedron Lett. 2005, 46, 8579-8581
54. L. Bethge, D. V. Jarikote, O. Seitz, Bioorg. Med. Chem. 2008, 16, 114-125