Divergent total synthesis of the antimitotic agent leiodermatolide

Angewandte Chemie - International Edition

Volumn 51, Issue 48, 2012, Pages 12041-12046

  Willwacher, Jens ^a   Kausch Busies, Nina ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

alkyne metathesis; antitumor agents; natural products; structure eludication; total synthesis

Indexed keywords

ALKYNE METATHESIS; ANTI-TUMOR AGENTS; ANTIMITOTIC AGENTS; H NMR SPECTRA; NATURAL PRODUCTS; RING CLOSINGS; STEREOSTRUCTURE; TOTAL SYNTHESIS;

ACETYLENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

MUTAGENESIS;

ALKYNE; ANTIMITOTIC AGENT; LEIODERMATOLIDE; MACROLIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; ANTIMITOTIC AGENTS; MACROLIDES; MOLECULAR STRUCTURE;

EID: 84870050740     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206670     Document Type: Article

References (57)

1. Anticancer Agents from Natural Products (Eds.:, G. M. Cragg, D. G. I. Kingston, D. J. Newman,), CRC, Boca Raton, FL, 2005.
2. K.-H. Altmann, J. Gertsch, Nat. Prod. Rep. 2007, 24, 327-357.
3. K. E. Gascoigne, S. S. Taylor, J. Cell Sci. 2009, 122, 2579-2585.
4. A. E. Wright, J. K. Reed, J. Roberts, R. E. Longley, U.S. Pat. Appl. US 20080033035A1 20080207, 2008.
5. I. Paterson, S. M. Dalby, J. C. Roberts, G. J. Naylor, E. A. Guzmán, R. Isbrucker, T. P. Pitts, P. Linley, D. Divlianska, J. K. Reed, A. E. Wright, Angew. Chem. 2011, 123, 3277-3281
6. Angew. Chem. Int. Ed. 2011, 50, 3219-3223.
7. J. S. Sandler, P. L. Colin, M. Kelly, W. Fenical, J. Org. Chem. 2006, 71, 7245-7251; correction
8. J. S. Sandler, P. L. Colin, M. Kelly, W. Fenical, J. Org. Chem. 2006, 71, 8684.
9. A. Larivée, J. B. Unger, M. Thomas, C. Wirtz, C. Dubost, S. Handa, A. Fürstner, Angew. Chem. 2011, 123, 318-323
10. Angew. Chem. Int. Ed. 2011, 50, 304-309.
11. A truncated macrocyclic core of type A terminated by an alkenyl bromide was recently prepared, but no attempts to attach the side chain through cross-coupling were reported, see, I. Paterson, T. Paquet, S. M. Dalby, Org. Lett. 2011, 13, 4398-4401.
12. For a non-natural diastereomer of the macrocycle, see, C. Rink, V. Navickas, M. E. Maier, Org. Lett. 2011, 13, 2334-2337.
13. V. Navickas, C. Rink, M. E. Maier, Synlett 2011, 191-194.
14. A. Fürstner, Angew. Chem. 2012, DOI:;
15. Angew. Chem. Int. Ed. 2012, DOI:.
16. A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760
17. Angew. Chem. Int. Ed. 1998, 37, 1734-1736
18. A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307-2320.
19. For a discussion, see, D. Gallenkamp, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 9232-9235 and the references therein.
20. K. Micoine, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 14064-14066
21. A. Fürstner, L. Turet, Angew. Chem. 2005, 117, 3528-3532
22. Angew. Chem. Int. Ed. 2005, 44, 3462-3466
23. A. Fürstner, D. DeSouza, L. Turet, M. D. B. Fenster, L. Parra-Rapado, C. Wirtz, R. Mynott, C. W. Lehmann, Chem. Eur. J. 2007, 13, 115-134
24. A. Fürstner, M. Bonnekessel, J. T. Blank, K. Radkowski, G. Seidel, F. Lacombe, B. Gabor, R. Mynott, Chem. Eur. J. 2007, 13, 8762-8783.
25. R. Baker, J. L. Castro, J. Chem. Soc. Perkin Trans. 1 1990, 47-65.
26. A. Abiko, J.-F. Liu, S. Masamune, J. Am. Chem. Soc. 1997, 119, 2586-2587
27. T. Inoue, J.-F. Liu, D. C. Buske, A. Abiko, J. Org. Chem. 2002, 67, 5250-5256
28. A. Fürstner, J. Ruiz-Caro, H. Prinz, H. Waldmann, J. Org. Chem. 2004, 69, 459-467.
29. This reaction has precedent, see, D. Menche, J. Hassfeld, J. Li, K. Mayer, S. Rudolph, J. Org. Chem. 2009, 74, 7220-7229; however, we invariably obtained a somewhat lower selectivity (anti/syn=13:1 versus >20:1 in the literature).
30. C. Bonini, L. Chiummiento, V. Videtta, Synlett 2005, 3067-3070
31. C. Bonini, L. Chiummiento, V. Videtta, Synlett 2006, 2079-2082
32. D. A. Evans, H. P. Ng, J. S. Clark, D. L. Rieger, Tetrahedron 1992, 48, 2127-2142.
33. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560-3578.
34. I. Kuwajima, Y. Doi, Tetrahedron Lett. 1972, 13, 1163-1166.
35. K. Hinterding, S. Singhanat, L. Oberer, Tetrahedron Lett. 2001, 42, 8463-8465.
36. Review:, J. Augé, N. Lubin-Germain, J. Uziel, Synthesis 2007, 1739-1764.
37. G. W. Kramer, H. C. Brown, J. Org. Chem. 1977, 42, 2292-2299.
38. E. Canales, K. G. Prasad, J. A. Soderquist, J. Am. Chem. Soc. 2005, 127, 11572-11573.
39. B. E. Uno, E. P. Gillis, M. D. Burke, Tetrahedron 2009, 65, 3130-3138.
40. J. Heppekausen, R. Stade, R. Goddard, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11045-11057
41. J. Heppekausen, R. Stade, A. Kondoh, G. Seidel, R. Goddard, A. Fürstner, Chem. Eur. J. 2012, 18, 10281-10299.
42. A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317
43. A. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453-9454.
44. A. Suzuki, Angew. Chem. 2011, 123, 6854-6869
45. Angew. Chem. Int. Ed. 2011, 50, 6722-6737.
46. J. Uenishi, J.-M. Beau, R. W. Armstrong, Y. Kishi, J. Am. Chem. Soc. 1987, 109, 4756-4758
47. S. A. Frank, H. Chen, R. K. Kunz, M. J. Schnaderbeck, W. R. Roush, Org. Lett. 2000, 2, 2691-2694.
48. W. Boland, N. Schroer, C. Sieler, M. Feigel, Helv. Chim. Acta 1987, 70, 1025-1040.
49. P. Kočovský, Tetrahedron Lett. 1986, 27, 5521-5524.
50. Y. Quindon, H. E. Morton, C. Yoakim, Tetrahedron Lett. 1983, 24, 3969-3972
51. Y. Guindon, C. Yoakim, H. E. Morton, J. Org. Chem. 1984, 49, 3912-3920.
52. W. Chaładaj, M. Corbet, A. Fürstner, Angew. Chem. 2012, 124, 7035-7039
53. Angew. Chem. Int. Ed. 2012, 51, 6929-6933
54. V. Hickmann, A. Kondoh, B. Gabor, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471-13480
55. K. Lehr, R. Mariz, L. Leseurre, B. Gabor, A. Fürstner, Angew. Chem. 2011, 123, 11575-11579
56. Angew. Chem. Int. Ed. 2011, 50, 11373-11377.
57. For another study from our research group illustrating this notion, see, A. Fürstner, M. Albert, J. Mlynarski, M. Matheu, E. DeClercq, J. Am. Chem. Soc. 2003, 125, 13132-13142.