An organocatalytic asymmetric allylic alkylation allows enantioselective total synthesis of hydroxymetasequirin-a and metasequirin-b tetramethyl ether diacetates

Organic Letters

Volumn 16, Issue 3, 2014, Pages 976-979

  Wang, Pu Sheng ^a   Zhou, Xiao Le ^a   Gong, Liu Zhu ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84893841468     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4037055     Document Type: Article

References (63)

1. Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 6, 4387
2. Trost, B. M.; Fullerton, T. J. J. Am. Chem. Soc. 1973, 95, 292
3. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395
4. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1
5. Trost, B. M. J. Org. Chem. 2004, 69, 5813
6. Falciola, C. A.; Alexakis, A. Eur. J. Org. Chem. 2008, 3765
7. Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258
8. Trost, B. M. Org. Process Res. Dev. 2012, 16, 185
9. Trost, B. M. Acc. Chem. Res. 1996, 29, 355
10. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921
11. Trost, B. M.; Fandrick, D. R. Aldrichimica Acta 2007, 40, 59
12. Rios, I. G.; Rosas-Hernandez, A.; Martin, E. Molecules 2011, 16, 970
13. Hong, A. Y.; Stoltz, B. M. Eur. J. Org. Chem. 2013, 2745
14. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726
15. Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719
16. Lelais, G.; MacMillan, D. W. C. Aldrichimica Acta 2006, 39, 79
17. Pellissier, H. Tetrahedron 2007, 63, 9267
18. Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471
19. Barbas, C. F., III. Angew. Chem., Int. Ed. 2008, 47, 42
20. MacMillan, D. W. C. Nature 2008, 455, 304
21. Bertelsen, S.; Jørgensen, K. A. Chem. Soc. Rev. 2009, 38, 2178
22. Stary, I.; Stará, G.; Kocoîvsky, P. Tetrahedron Lett. 1993, 34, 179
23. Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968
24. García-Yebra, C.; Janssen, J. P.; Rominger, F.; Helmchen, G. Organometallics 2004, 23, 5459
25. Kimura, M.; Futamata, M.; Mukai, R.; Tamaru, Y. J. Am. Chem. Soc. 2005, 127, 4592
26. Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314
27. Yamashita, Y.; Gopalarathnam, A.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7508
28. Usui, I.; Schmidt, S.; Breit, B. Org. Lett. 2009, 11, 1453
29. Jiang, G. X.; List, B. Angew. Chem., Int. Ed. 2011, 50, 9471
30. Yasuda, S.; Kumagai, N.; Shibasaki, M. Heterocycles 2012, 86, 745
31. Krautwald, S.; Sarlah, D.; Schafroth, M. A.; Carreira, E. M. Science 2013, 340, 1065
32. Hamilton, J. Y.; Sarlah, D.; Carreira, E. M. J. Am. Chem. Soc. 2013, 135, 994
33. Tao, Z. L.; Zhang, W. Q.; Chen, D. F.; Adele, A.; Gong, L. Z. J. Am. Chem. Soc. 2013, 135, 9255
34. Rueping, M.; Nachtsheim, B. J. Beilstein J. Org. Chem. 2010, 6, 1
35. Emer, E.; Sinisi, R.; Capdevila, M. G.; Petruzziello, D.; De Vincentiis, F.; Cozzi, P. G. Eur. J. Org. Chem. 2011, 647
36. Rueping, M.; Uria, U.; Lin, M.-Y.; Atodiresei, I. J. Am. Chem. Soc. 2011, 133, 3732
37. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
38. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356
39. Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
40. Terada, M. Chem. Commun. 2008, 4097
41. Adair, G.; Mukherjee, S.; List, B. Aldrichimica Acta 2008, 41, 31
42. Terada, M. Synthesis 2010, 1929
43. Terada, M. Bull. Chem. Soc. Jpn. 2010, 101
44. Yu, J.; Shi, F.; Gong, L. Z. Acc. Chem. Res. 2011, 44, 1156
45. Avila, E. P.; Amarante, G. W. ChemCatChem 2012, 4, 1713
46. Brière, J. F.; Oudeyer, S.; Dallab, V.; Levacher, V. Chem. Soc. Rev. 2012, 41, 1696
47. Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nat. Chem. 2012, 4, 603
48. Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534
49. Mahlau, M.; List, B. Angew. Chem., Int. Ed. 2013, 52, 518
50. Enoki, A.; Takahama, S.; Kitao, K. Mokuzai Gakkaishi 1977, 23, 587
51. Sancéau, J. Y.; Dhal, R.; Brown, E. Tetrahedron 1994, 50, 3363
52. Kramer, B.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2004, 43, 2446
53. Hackelöer, K.; Schnakenburg, G.; Waldvogel, S. R. Eur. J. Org. Chem. 2011, 6314
54. Hackelöer, K.; Schnakenburg, G.; Waldvogel, S. R. Org. Lett. 2011, 13, 916
55. Hackelöer, K.; Waldvogel, S. R. Tetrahedron Lett. 2012, 53, 1579
56. Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroeder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968
57. Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547
58. Vedejs, E. J. Am. Chem. Soc. 1974, 96, 5944
59. Taschner, M. J.; Aminbhavi, A. S. Tetrahedron Lett. 1989, 30, 1029
60. Campeau, L. C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581
61. Bringmann, G.; Gulder, T.; Gulder, T. A. M.; Breuning, M. Chem. Rev. 2011, 111, 563
62. Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960
63. Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2013, 52, 7865