Total synthesis of tulearin C

Angewandte Chemie - International Edition

Volumn 50, Issue 48, 2011, Pages 11373-11377

  Lehr, Konrad ^a   Mariz, Ronaldo ^a   Leseurre, Lucie ^a   Gabor, Barbara ^a   Fürstner, Alois ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

alkyne metathesis; alkynes; hydrosilylation; natural products; total synthesis

Indexed keywords

ALKENE METATHESIS; ALKYNE METATHESIS; ALKYNES; MACROLIDES; NATURAL PRODUCTS; RING CLOSINGS; TOTAL SYNTHESIS;

HYDROSILYLATION; OLEFINS;

ACETYLENE;

ALKYNE; LACTONE; MACROLIDE; TULEARIN;

ARTICLE; CHEMISTRY; HUMAN; SYNTHESIS;

ALKYNES; HUMANS; LACTONES; MACROLIDES;

EID: 81755183001     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201106117     Document Type: Article

References (82)

1. Handbook of Metathesis, Vol.1-3 (Ed.:, R.H. Grubbs,), Wiley-VCH, Weinheim, 2003
2. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564-4601
3. Angew. Chem. Int. Ed. 2005, 44, 4490-4527
4. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243-251
5. A. Fürstner, Chem. Commun. 2011, 47, 6505-6511
6. J. Prunet, Angew. Chem. 2003, 115, 2932-2936
7. Angew. Chem. Int. Ed. 2003, 42, 2826-2830.
8. A. Fürstner, Angew. Chem. 2000, 112, 3140-3172
9. Angew. Chem. Int. Ed. 2000, 39, 3012-3043
10. A. Fürstner, K. Langemann, Synthesis 1997, 792-803
11. A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943.
12. S. J. Meek, R. V. O'Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda, Nature 2011, 471, 461-466
13. A. J. Jiang, Y. Zhao, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 16630-16631
14. K. Endo, R. H. Grubbs, J. Am. Chem. Soc. 2011, 133, 8525-8527, and references therein.
15. A non-natural isomer had been targeted in this study because the correct stereostructure of tulearinA was disclosed only after the synthesis had been completed, see:, A. L. Mandel, V. Bellosta, D. P. Curran, J. Cossy, Org. Lett. 2009, 11, 3282-3285.
16. D. Meng, D.-S. Su, A. Balog, P. Bertinato, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zeng, T.-C. Chou, L. He, S. B. Horwitz, J. Am. Chem. Soc. 1997, 119, 2733-2734
17. A. Fürstner, T. Dierkes, O. R. Thiel, G. Blanda, Chem. Eur. J. 2001, 7, 5286-5298.
18. A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760
19. Angew. Chem. Int. Ed. 1998, 37, 1734-1736
20. A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113.
21. A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307-2320
22. W. Zhang, J. S. Moore, Adv. Synth. Catal. 2007, 349, 93-120
23. R. R. Schrock, C. Czekelius, Adv. Synth. Catal. 2007, 349, 55-77.
24. J. Heppekausen, R. Stade, R. Goddard, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11045-11057
25. M. Bindl, R. Stade, E. K. Heilmann, A. Picot, R. Goddard, A. Fürstner, J. Am. Chem. Soc. 2009, 131, 9468-9470.
26. A. Bishara, A. Rudi, I. Goldberg, M. Aknin, Y. Kashman, Tetrahedron Lett. 2009, 50, 3820-3822
27. A. Bishara, A. Rudi, M. Aknin, D. Neumann, N. Ben-Califa, Y. Kashman, Org. Lett. 2008, 10, 153-156.
28. L. K. P. Lam, R. A. H. F. Hui, J. B. Jones, J. Org. Chem. 1986, 51, 2047-2050
29. L. Poppe, L. Novák, P. Kolonits, à. Bata, C. Szántay, Tetrahedron 1988, 44, 1477-1487.
30. M. Lakhrissi, Y. Chapleur, J. Org. Chem. 1994, 59, 5752-5757.
31. J. S. Yadav, V. Prahlad, M. C. Chander, J. Chem. Soc. Chem. Commun. 1993, 137-138
32. J. S. Yadav, C. Venugopal, Synlett 2007, 2262-2266.
33. We are aware of only one example in which a gem-diiodo-alkenyl ether was directly transformed into a nonterminal alkyne, see:, R. M. Black, G. B. Gill, J. Chem. Soc. Perkin Trans. 1 1980, 410-418.
34. G. Köbrich, F. Ansari, Chem. Ber. 1967, 100, 2011-2020
35. M. Duraisamy, H. M. Walborsky, J. Am. Chem. Soc. 1984, 106, 5035-5037
36. M. Topolski, M. Duraisamy, J. Rachon, J. Gawronski, K. Gawronska, V. Goedken, H. M. Walborsky, J. Org. Chem. 1993, 58, 546-555.
37. For deprotonations of carbohydrate-derived dichloroolefins, see:, A. Bandzouzi, Y. Chapleur, Carbohydr. Res. 1987, 171, 13-24.
38. D. Boyall, D. E. Frantz, E. M. Carreira, Org. Lett. 2002, 4, 2605-2606
39. D. E. Frantz, R. Fässler, E. M. Carreira, J. Am. Chem. Soc. 2000, 122, 1806-1807.
40. S. E. Denmark, T. K. Jones, J. Org. Chem. 1982, 47, 4595-4597.
41. E. Negishi, Bull. Chem. Soc. Jpn. 2007, 80, 233-257.
42. X. Zeng, M. Qian, Q. Hu, E. Negishi, Angew. Chem. 2004, 116, 2309-2313
43. Angew. Chem. Int. Ed. 2004, 43, 2259-2263
44. K. C. Nicolaou, A. L. Nold, R. R. Milburn, C. S. Schindler, Angew. Chem. 2006, 118, 6677-6682
45. Angew. Chem. Int. Ed. 2006, 45, 6527-6532.
46. J. Madec, X. Pfister, P. Phansavath, V. Ratovelomanana-Vidal, J.-P. Genêt, Tetrahedron 2001, 57, 2563-2568
47. C. Roche, N. Desroy, M. Haddad, P. Phansavath, J.-P. Genêt, Org. Lett. 2008, 10, 3911-3914.
48. G. Fráter, U. Müller, W. Günther, Tetrahedron 1984, 40, 1269-1277
49. D. Seebach, J. Aebi, D. Wasmuth, Org. Synth. 1985, 63, 109-119.
50. Y. Tamaru, H. Ochiai, T. Nakamura, K. Tsubaki, Z. Yoshida, Tetrahedron Lett. 1985, 26, 5559-5562
51. Y. Tamaru, H. Ochiai, T. Nakamura, Z. Yoshida, Tetrahedron Lett. 1986, 27, 955-958
52. C. Aassa, R. Riveiros, J. Ragot, A. Fürstner, J. Am. Chem. Soc. 2003, 125, 15512-15520.
53. Z. Huang, E. Negishi, Org. Lett. 2006, 8, 3675-3678.
54. R. A. Johnson, K. B. Sharpless, in Catalytic Asymmetric Synthesis, 2 nd ed., (Ed.: I. Ojima,), Wiley-VCH, New York, 2000, pp. 357-398.
55. V. Hickmann, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11042-11044
56. V. Hickmann, A. Kondoh, B. Gabor, M. Alcarazo, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471-13480.
57. B. M. Trost, Z. T. Ball, T. Jöge, J. Am. Chem. Soc. 2002, 124, 7922-7923
58. B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2001, 123, 12726-12727
59. B. M. Trost, Z. T. Ball, Synthesis 2005, 853-887.
60. A. Fürstner, K. Radkowski, Chem. Commun. 2002, 2182-2183
61. F. Lacombe, K. Radkowski, G. Seidel, A. Fürstner, Tetrahedron 2004, 60, 7315-7324
62. A. Fürstner, M. Bonnekessel, J. T. Blank, K. Radkowski, G. Seidel, F. Lacombe, B. Gabor, R. Mynott, Chem. Eur. J. 2007, 13, 8762-8783.
63. K. Micoine, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 14064-14066.
64. A. Fürstner, K. Grela, C. Mathes, C. W. Lehmann, J. Am. Chem. Soc. 2000, 122, 11799-11805
65. A. Fürstner, K. Radkowski, J. Grabowski, C. Wirtz, R. Mynott, J. Org. Chem. 2000, 65, 8758-8762
66. A. Fürstner, C. Mathes, K. Grela, Chem. Commun. 2001, 1057-1059
67. A. Fürstner, L. Turet, Angew. Chem. 2005, 117, 3528-3532
68. Angew. Chem. Int. Ed. 2005, 44, 3462-3466
69. A. Fürstner, M. Bindl, L. Jean, Angew. Chem. 2007, 119, 9435-9438
70. Angew. Chem. Int. Ed. 2007, 46, 9275-9278
71. 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
72. V. V. Vintonyak, M. E. Maier, Angew. Chem. 2007, 119, 5301-5303
73. Angew. Chem. Int. Ed. 2007, 46, 5209-5211
74. B. J. Smith, G. A. Sulikowski, Angew. Chem. 2010, 122, 1643-1646
75. Angew. Chem. Int. Ed. 2010, 49, 1599-1602
76. M. G. Nilson, R. L. Funk, Org. Lett. 2010, 12, 4912-4915
77. A. F. Kyle, P. Jakubec, D. M. Cockfield, E. Cleator, J. Skidmore, D. J. Dixon, Chem. Commun. 2011, 47, 10037-10039.
78. A. Fürstner, A.-S. Castanet, K. Radkowski, C. W. Lehmann, J. Org. Chem. 2003, 68, 1521-1528
79. A. Fürstner, O. Larionov, S. Flügge, Angew. Chem. 2007, 119, 5641-5644
80. Angew. Chem. Int. Ed. 2007, 46, 5545-5548
81. S. Benson, M.-P. Collin, A. Arlt, B. Gabor, R. Goddard, A. Fürstner, Angew. Chem. 2011, 123, 8898-8903
82. Angew. Chem. Int. Ed. 2011, 50, 8739-8744.