Concise and practical synthesis of latrunculin A by ring-closing enyne-yne metathesis

Angewandte Chemie - International Edition

Volumn 44, Issue 22, 2005, Pages 3462-3466

  Fürstner, Alois ^a   Turet, Laurent ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Alkynes; Cross coupling; Macrocycles; Metathesis; Natural products

Indexed keywords

BIOCHEMISTRY; CATALYSIS; CHEMICAL BONDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

LATRUNCULIN A; MARINE NATURAL PRODUCTS; METATHESIS; SELECTIVE ACTIN BINDING;

ORGANIC COMPOUNDS;

ALKYNE; FUSED HETEROCYCLIC RINGS; LATRUNCULIN A; THIAZOLE DERIVATIVE; THIAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKYNES; BICYCLO COMPOUNDS, HETEROCYCLIC; CYCLIZATION; MOLECULAR STRUCTURE; THIAZOLES; THIAZOLIDINES;

EID: 20444381357     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500390     Document Type: Article

References (60)

1. Isolation: a) I. Neeman, L. Fishelson, Y. Kashman, Mar. Biol. 1975, 30, 293-296;
2. b) A. Groweiss, U. Shmueli, Y. Kashman, J. Org. Chem. 1983, 48, 3512-3516;
3. c) Y. Kashman, A. Groweiss, R. Lidor, D. Blasberger, S. Carmely, Tetrahedron 1985, 41, 1905-1914;
4. d) R. K. Okuda, P. J. Scheuer, Experientia 1985, 41, 1355-1356;
5. e) Y. Kakou, P. Crews, G. J. Bakus, J. Nat. Prod. 1987, 50, 482-484;
6. f) N. K. Gulavita, S. P. Gunasekera, S. A. Pomponi, J. Nat. Prod. 1992, 55, 506-508;
7. g) J. Tanaka, T. Higa, G. Bernardinelli, C. W. Jefford, Chem. Lett. 1996, 255-256;
8. h) D. Mebs, J. Chem. Ecol. 1985, 11, 713-716;
9. i) T. R. Hoye, S.-E. N. Ayyad, B. M. Eklov, N. E. Hashish, W. T. Shier, K. A. El Sayed, M. T. Hamann, J. Am. Chem. Soc. 2002, 124, 7405-7410.
10. I. Spector, N. R. Shochet, Y. Kashman, A. Groweiss, Science 1983, 219, 493-495.
11. Selected reviews: a) K.-S. Yeung, I. Paterson, Angew. Chem. 2002, 114, 4826-4847;
12. Angew. Chem. Int. Ed. 2002, 41, 4632-4653;
13. b) J. R. Peterson, T. J. Mitchison, Chem. Biol. 2002, 9, 1275-1285;
14. c) I. Spector, N. R. Shochet, D. Blasberger, Y. Kashman, Cell Motil. Cytoskeleton 1989, 13, 127-144;
15. d) W. M. Morton, K. R. Ayscough, P. J. McLaughlin, Nat. Cell Biol. 2000, 2, 376-378, and references therein.
16. a) Y. Gachet, S. Tournier, J. B. A. Millar, J. S. Hyams, Nature 2001, 412, 352-355;
17. b) see also: Y. Nakaseko, M. Yanagida, Nature 2001, 412, 291-292.
18. a) A. B. Smith, J. W. Leahy, I. Noda, S. W. Remiszewski, N. J. Liverton, R. Zibuck, J. Am. Chem. Soc. 1992, 114, 2995-3007;
19. b) A. B. Smith, I. Noda, S. W. Remiszewski, N. J. Liverton, R. Zibuck, J. Org. Chem. 1990, 55, 3977-3979;
20. c) R. Zibuck, N. J. Liverton, A. B. Smith, J. Am. Chem. Soc. 1986, 108, 2451-2453.
21. a) J. D. White, M. Kawasaki, J. Org. Chem. 1992, 57, 5292-5300;
22. b) J. D. White, M. Kawasaki, J. Am. Chem. Soc. 1990, 112, 4991-4993.
23. A. Fürstner, D. De Souza, L. Parra-Rapado, J. T. Jensen, Angew. Chem. 2003, 115, 5516-5518;
24. Angew. Chem. Int. Ed. 2003, 42, 5358-5360.
25. a) A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760;
26. Angew. Chem. Int. Ed. 1998, 37, 1734-1736;
27. b) A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113.
28. A. Fürstner, P. W. Davies, Chem. Commun., in press.
29. In this context, it is worth mentioning that standard alkene metathesis catalysts do not distinguish between alkenes and alkynes, but attack both types of π systems with similar ease. For example, see: a) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382;
30. b) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
31. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
32. F. Lacombe, K. Radkowski, G. Seidel, A. Fürstner, Tetrahedron 2004, 60, 7315-7324.
33. Similar observations were previously reported by Smith et al. in ref. [5], and Kashman and co-workers in: D. Blasberger, S. Carmely, M. Cojocaru, I. Spector, N. R. Shochet Y. Kashman, Liebigs Ann. Chem. 1989, 1171-1188.
34. I. Paterson, K.-S. Yeung, J. B. Smaill, Synlett 1993, 774-776.
35. 2O is significantly more productive (82%) and readily scaleable (8 g).
36. B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943-3949.
37. a) A. Fürstner, A. Leitner, M. Méndez, H. Krause, J. Am. Chem. Soc. 2002, 124, 13856-13863;
38. b) A. Fürstner, A. Leitner, Angew. Chem. 2002, 114, 632-635;
39. Angew. Chem. Int. Ed. 2002, 41, 609-612;
40. c) A. Fürstner, A. Leitner, Angew. Chem. 2003, 115, 320-323;
41. Angew. Chem. Int. Ed. 2003, 42, 308-311;
42. d) B. Scheiper, F. Glorius, A. Leitner, A. Fürstner, Proc. Natl. Acad. Sci. USA 2004, 101, 11960-11965;
43. e) R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045-4047;
44. Angew. Chem. Int. Ed. 2004, 43, 3955-3957;
45. f) A. Fürstner, R. Martin, Chem. Lett. 2005, 34, 624-628.
46. A more direct approach to 19 by cross-coupling of enol triflate 12 with bromide 29 was unsuccessful as the latter could not be converted into the corresponding Grignard reagent. (Chemical Equation Presented)
47. a) S. Ohira, Synth. Commun. 1989, 19, 561-564;
48. b) S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521-522.
49. J. Schwartz, J. A. Labinger, Angew. Chem. 1976, 88, 402-409;
50. Angew. Chem. Int. Ed. Engl. 1976, 15, 333-340.
51. 2, furnished an inseparable mixture of the E and Z isomers, details of which will be reported in a forthcoming full paper.
52. a) A. Fürstner, G. Seidel, Tetrahedron 1995, 51, 11165-11176;
53. b) for a recent application, see: O. Lepage, E. Kattnig, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 15970-15971.
54. a) A. Fürstner, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 1999, 121, 9453-9454;
55. b) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5299-5317.
56. Previous applications: a) A. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11799-11805;
57. b) A. Fürstner, K. Radkowski, J. Grabowski, C. Wirtz, R. Mynott, J. Org. Chem. 2000, 65, 8758-8762;
58. c) A. Fürstner, C. Mathes, K. Grela, Chem. Commun. 2001, 1057-1059;
59. d) A. Fürstner, F. Stelzer, A. Rumbo, H. Krause, Chem. Eur. J. 2002, 8, 1856-1871.
60. Smith et al. reported that they failed to deprotect the N-PMB group from the corresponding macrocyclic diene prepared by an entirely different route (see ref. [5]).