Convergent synthesis of fostriecin via selective alkene couplings and regioselective asymmetric dihydroxylation

Organic Letters

Volumn 11, Issue 23, 2009, Pages 5498-5501

  Robles, Omar ^a   McDonald, Frank E ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FOSTRIECIN; PALLADIUM; PYRONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; PYRONES; STEREOISOMERISM;

EID: 72449164433     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902365n     Document Type: Article

References (52)

1. (a) Tunac, J. B.; Graham, B. D.; Dobson, W. E. J. Antibiot. 1983, 36, 1595.
2. (b) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C. E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601.
3. Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748.
4. Review : Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005.
5. Hastie, C. J.; Cohen, P. T. W. FEBS Lett. 1998, 431, 357.
6. (a) Boger, D. L.; Ichikawa, S.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161.
7. (b) Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667.
8. Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969.
9. Esumi, T.; Okamoto, N.; Hatakeyama, S. Chem. Commun. 2002, 3042.
10. (e) Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. J. Am. Chem. Soc. 2003, 125, 8238.
11. (f) Maki, K.; Motoki, R.; Fujii, K.; Kanai, M.; Kobayashi, T.; Tamura, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 17111.
12. (g) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233.
13. (h) Wang, Y. G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615.
14. Trost, B. M.; Frederiksen, M. U.; Papillon, J. P. N.; Harrington, P. E.; Shin, S.; Shireman, B. T. J. Am. Chem. Soc. 2005, 127, 3666.
15. (j) Hayashi, Y.; Yamaguchi, H.; Toyoshima, M.; Okado, K.; Toyo, T.; Shoji, M. Org. Lett. 2008, 10, 1405. Review:
16. (k) Shibasaki, M.; Kanai, M. Heterocycles 2005, 66, 727.
17. (a) Shimada, K.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 4048.
18. (b) Bialy, L.; Waldmann, H. Chem.-Eur. J. 2004, 10, 2759.
19. Wang, Y.-G.; Takeyama, R.; Kobayashi, Y. Angew. Chem., Int. Ed 2006, 45, 3320.
20. Lawhom, B. G.; Boga, S. B.; Wolkenberg, S. E.; Colby, D. A.; Gauss, C.-M.; Swingle, M. R.; Amable, L.; Honkanen, R. E.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 16720.
21. (e) Shibahara, S.; Fujino, M.; Tashiro, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Org. Lett. 2008, 10, 2139.
22. (f) Miyashita, K.; Tsunemi, T.; Hosokawa, T.; Ikejiri, M.; Imanishi, T. J. Org. Chem. 2008, 73, 5360.
23. (g) Draais, V.; Hall, M. J.; Corsi, C.; Wendeborn, S. V.; Meyer, C.; Cossy, J. J. Org. Lett. 2009, 11, 935.
24. (h) König, C. M.; Gebhardt, B.; Schleth, C.; Dauber, M.; Koert, U. Org. Lett. 2009, 11, 2728.
25. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
26. Enynols (R)-5 and (A)-10 were prepared by lipase-catalyzed resolution, of the racemic compounds with vinyl acetate followed by Mitsunobu reaction of the resolved alcohols into the antipodal acetates for efficient production of a single enantiomer from the racemate: (a) Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
27. (b) Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2002, 124, 8188.
28. Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2004, 126, 2495.
29. Langille, N. F.; Panek, J. S. Org. Lett. 2004, 6, 3203.
30. (e) Robles, O.; McDonald, F. E. Org. Lett. 2008, 10, 1811.
31. (a) Ahmed, A.; Hoegenauer, E. K.; Enev, V. S.; Hanbauer, M.; Kaehlig, H.; Öhler, E.; Mulzer, J. J. Org. Chem. 2003, 68, 3026.
32. (b) Crimmins, M. T.; King, B. W. J. Am. Chem. Soc. 1998, 120, 9084.
33. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
34. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
35. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
36. (a) Negishi, E.-i.; Hu, Q.; Huang, Z.; Qian, M.; Wang, G. Aldrichim. Acta 2005, 38, 71.
37. -: Srogl, J.; Allred, G.; Liebeskind, L. S. J. Am. Chem. Soc. 1997, 119, 12376.
38. Huang, Z.; Negishi, E.-i. Org. Lett. 2006, 8, 3675.
39. Buchwald, S. L.; Lamaire, S. J.; Nelson, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
40. Zeng, X.; Qian, M.; Hu, Q.; Negishi, E.-i. Angew. Chem., Int. Ed. 2004, 43, 2259.
41. Shi, J.-c.; Zeng, X.; Negishi, E.-i. Org. Lett. 2003, 5, 1825.
42. (a) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis. 1994, 639.
43. 2 oxidation of the hemiacetal precursor in slightly lower yield.
44. (a) Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lübben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56, 4585.
45. (b) Kolb, H. C.; Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 1278.
46. Norrby, P.-O.; Becker, H.; Sharpless, K. B. J. Am. Chem. Soc. 1996, 118, 35.
47. (a) Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507.
48. (b) We observed reduction of the 2,3-alkene when more than 2 equiv of o-nitrobenzenesulfonylhydrazide was used.
49. Yields with silver oxide as the base varied from 31% (65 °C, 4 h) to 55% (20 °C, 8 days), whereas the reaction with thallium carbonate proceeded in 81% yield (20 °C, 8 h).
50. Uenishi, J.-i.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756.
51. (a) Buck, S. B.; Hardouin, C.; Ichikawa, S.; Soenen, D. R.; Gauss, C.-M.; Hwang, I.; Swingle, M. R.; Bonness, K. M.; Honkanen, R. E.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 15694.
52. (b) Chen, W.; Possemato, R.; Campbell, K. T.; Plattner, C. A.; Pallas, D. C.; Hahn, W. C. Cancer Cell 2004, 5, 127.