Biomimetic synthesis of (±)-merochlorin B

Organic Letters

Volumn 16, Issue 10, 2014, Pages 2634-2637

  Meier, Robin ^a   Strych, Sebastian ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IODINE; MEROCHLORIN B; SESTERTERPENE;

ARTICLE; BIOMIMETICS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

BIOMIMETICS; CYCLOADDITION REACTION; INDICATORS AND REAGENTS; IODINE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SESTERTERPENES; STEREOISOMERISM; STREPTOMYCES;

EID: 84900836581     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500800z     Document Type: Article

References (53)

1. Sakoulas, G.; Nam, S.-J.; Loesgen, S.; Fenical, W.; Jensen, P. R.; Nizet, V.; Hensler, M. PLoS One 2012, 7, e29439
2. Kaysser, L.; Bernhardt, P.; Nam, S.-J.; Loesgen, S.; Ruby, J. G.; Skewes-Cox, P.; Jensen, P. R.; Fenical, W.; Moore, B. S. J. Am. Chem. Soc. 2012, 134, 11988
3. Pepper, H. P.; George, J. H. Angew. Chem. 2013, 125, 12392
4. Angew. Chem., Int. Ed. 2013, 52, 12170.
5. Büchi, G.; Chu, P.-S. Tetrahedron 1981, 37, 4509
6. Grieco, P. A.; Walker, J. K. Tetrahedron 1997, 53, 8975
7. Engler, T. A.; Scheibe, C. M. J. Org. Chem. 1998, 63, 6247
8. Horne, D. A.; Yakushijin, K.; Büchi, G. Tetrahedron Lett. 1999, 40, 5443
9. Quideau, S.; Pouységu, L.; Deffieux, D. Curr. Org. Chem. 2004, 8, 113
10. Yamamura, S.; Nishiyama, S. Synlett 2002, 4, 533
11. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135
12. Wu, K.-L.; Wilkinson, S.; Reich, N. O.; Pettus, T. R. R. Org. Lett. 2007, 9, 5537
13. Zhao, J.-C.; Yu, S.-M.; Liu, Y.; Yao, Z.-J. Org. Lett. 2013, 15, 4300
14. Green, J. C.; Pettus, T. R. R. J. Am. Chem. Soc. 2011, 133, 1603
15. Wu, K.-L.; Mercado, E. V.; Pettus, T. R. R. J. Am. Chem. Soc. 2011, 133, 6114
16. Bycroft, B. W.; Roberts, J. C. J. Chem. Soc. 1962, 2063
17. Beekman, A. M.; Martinez, E. C.; Barrow, R. A. Org. Biomol. Chem. 2013, 11, 1109
18. Bycroft, B. W.; Roberts, J. C. J. Chem. Soc. 1963, 4868
19. Gonzalez-Bello, C.; Abell, C.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1997, 1017
20. McCulloch, M. W. B.; Barrow, R. A. Tetrahedron Lett. 2005, 46, 7619
21. Gschwend, M. W.; Rodriguez, H. R. Org. React. 1979, 26, 1
22. Slocum, D. W.; Jennings, C. A. J. Org. Chem. 1976, 41, 3653
23. Slocum, D. W.; Dumbris, S.; Brown, S.; Jackson, G.; LaMastus, R.; Mullins, E.; Ray, J.; Shelton, P.; Walstrom, A.; Wilcox, J. M.; Holman, R. W. Tetrahedron 2003, 59, 8275
24. Snieckus, V. Chem. Rev. 1990, 90, 879
25. Mani, N. S.; Jablonowski, J. A.; Jones, T. K. J. Org. Chem. 2004, 69, 8115
26. Mitasev, B.; Porco, J. A., Jr. Org. Lett. 2009, 11, 2285
27. Ager, D. J. Org. React. 1990, 38, 1
28. Van Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195
29. Gembus, V.; Poisson, T.; Oudeyer, S.; Marsais, F.; Levacher, V. Synlett 2009, 15, 2437
30. Andrey, O.; Glanzmann, C.; Landais, Y.; Parra-Papado, L. Tetrahedron 1997, 53, 2835
31. Greene, A. E.; Le Drian, C.; Crabbe, P. J. Org. Chem. 1980, 45, 2713
32. Tiseni, P. S.; Peters, R. Angew. Chem. 2007, 119, 5419
33. Angew. Chem., Int. Ed. 2007, 46, 5325.
34. Raikar, S. B.; Nuhant, P.; Delpech, B.; Marazano, C. Eur. J. Org. Chem. 2008, 1358
35. Clive, D. L. J.; Daigneault, S. J. Org. Chem. 1991, 56, 5285
36. Tanaka, T.; Kumamoto, T.; Ishikawa, T. Tetrahedron Lett. 2000, 41, 10229
37. Yamaguchi, S.; Kobayashi, M.; Harada, S.; Miyazawa, M.; Hirai, Y. Bull. Chem. Soc. Jpn. 2008, 81, 863
38. Yamada, S.; Takeshita, T.; Tanaka, J. Bull. Chem. Soc. Jpn. 1986, 59, 2901
39. Hoarau, C.; Pettus, T. R. R. Synlett 2003, 1, 127
40. Le Noble, W. J. Synthesis 1970, 1, 1
41. Kornblum, N.; Lurie, A. P. J. Am. Chem. Soc. 1959, 81, 2705
42. Bates, R. W.; Gabel, C. J. Tetrahedron Lett. 1993, 34, 3547
43. Wessely, F.; Lauterbach-Keil, G.; Sinwel, F. Monatsh. Chem. 1950, 81, 811
44. Wessely, F.; Sinwel, F. Monatsh. Chem. 1950, 81, 1055
45. Bachman, G. B.; Wittmann, J. W. J. Org. Chem. 1963, 28, 65
46. Buston, J. E. H.; Howell, H. J.; Moloney, M. G.; Manson, V. C.; Thompson, R. M. Main Group Met. Chem. 1998, 21, 51
47. Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235
48. Quideau, S.; Pouységu, L.; Deffieux, D. Synlett 2008, 4, 467
49. Silva, L. F., Jr.; Olofsson, B. Nat. Prod. Rep. 2011, 28, 1722
50. Koser, G. F.; Wettach, R. H.; Troup, J. M.; Frenz, B. A. J. Org. Chem. 1976, 41, 3609
51. Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365
52. Kitamura, T.; Furuki, R.; Taniguchi, H.; Stang, P. J. Tetrahedron Lett. 1990, 31, 703
53. Kitamura, T.; Furuki, R.; Taniguchi, H.; Stang, P. J. Tetrahedron 1992, 48, 7149