Influence of appended groups on the formation of 16-membered macrolactone core related to the plecomacrolides via diene-ene ring-closing metathesis

Synlett

Volumn , Issue 14, 2009, Pages 2361-2365

  Sun, Liang ^a,b   Feng, Gaofeng ^a,b   Guan, Yucui ^a,b   Liu, Yuanxin ^a   Wu, Jinlong ^a,b   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

1,3 diene; Alkene; Macrolactone; Plecomacrolide; Ring closing metathesis

Indexed keywords

24 DEMETHYLBAFILOMYCIN A2; 24 DEMETHYLBAFILOMYCIN C1; BAFILOMYCIN A1; LACTONE DERIVATIVE; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; RING CLOSING METATHESIS; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 69449091831     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217720     Document Type: Article

References (60)

1. Werner, G.; Hagenmaier, H.; Drautz, H.; Baumgartner, A.; Zähner, H. J. Antibiot. 1984, 37, 110.
2. Bindseil, K. U.; Zeeck, A. Liebigs Ann. Chem. 1994, 305.
3. Dai, W.-M.; Guan, Y.; Jin, J. Curr. Med. Chem. 2005, 12, 1947.
4. (a) Kinashi, H.; Someno, K.; Sakaguchi, K.; Higashijima, T.; Miyazawa, T. Tetrahedron Lett. 1981, 22, 3857.
5. (b) Westley, J. W.; Liu, C. M.; Sello, L. H.; Evans, R. H.; Troupe, N.; Blount, J. F.; Chiu, A. M.; Todaro, L. J.; Miller, P. A. J. Antibiot. 1984, 37, 1738.
6. (c) Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R.; Ley, S. V.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron Lett. 1987, 28, 5565.
7. (d) Baker, G. H.; Brown, P. J.; Dorgan, R. J. J.; Everett, J. R. J. Chem. Soc., Perkin Trans. 2 1989, 1073.
8. (e) Dröse, S.; Bindseil, K. U.; Bowman, E. J.; Sievers, A.; Zeeck, A.; Altendorf, K. Biochemistry 1993, 32, 3902.
9. (f) Dröse, S.; Boddien, C.; Gassel, M.; Ingenhorst, G.; Zeeck, A.; Altendorf, K. Biochemistry 2001, 40, 2816.
10. Yoshimoto, Y.; Jyojima, T.; Arita, T.; Ueda, M.; Imoto, M.; Matsumura, S.; Toshima, K. Bioorg. Med. Chem. Lett. 2002, 12, 2525.
11. (a) Bowman, E. J.; Siebers, A.; Altendorf, K. Proc. Nat. Acad. Sci. U.S.A. 1988, 85, 7972.
12. (b) Drose, S.; Altendorf, K. J. Exp. Biol. 1997, 200, 1.
13. Bowman, B. J.; McCall, M. E.; Baertsch, R.; Bowman, E. J. J. Biol. Chem. 2006, 281, 31885.
14. For a review, see: Beutler, J. A.; McKee, T. C. Curr. Med. Chem. 2003, 10, 787.
15. (a) Lu, C.; Shen, Y. J. Antibiot. 2004, 57, 597.
16. (b) Lu, C.; Shen, Y. J. Antibiot. 2003, 56, 415.
17. (a) Evans, D. A.; Calter, M. A. Tetrahedron Lett. 1993, 34, 6871.
18. (b) Calter, M. A. PhD Thesis; Harvard University: USA, 1993.
19. (a) Toshima, K.; Jyokaaki, T.; Yamaguchi, H.; Murase, H.; Yoshida, T.; Mastumura, S.; Nakata, M. Tetrahedron Lett. 1996, 37, 1069.
20. (b) Toshima, K.; Yamaguchi, H.; Jyojima, T.; Noguchi, Y.; Nakata, M.; Mastumura, S. Tetrahedron Lett. 1996, 37, 1073.
21. (c) Toshima, K.; Jyojima, T.; Yamaguchi, H.; Noguchi, Y.; Yoshida, T.; Murase, H.; Nakata, M.; Mastumura, S. J. Org. Chem. 1997, 62, 3271.
22. (a) Scheidt, K. A.; Tasaka, A.; Bannister, T. D.; Wendt, M. D.; Roush, W. R. Angew. Chem. Int. Ed. 1999, 38, 1652.
23. (b) Scheidt, K. A.; Bannister, T. D.; Tasaka, A.; Wendt, M. D.; Savall, B. M.; Fegley, G. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 6981.
24. Hanessian, S.; Ma, J.; Wang, W.; Gai, Y. J. Am. Chem. Soc. 2001, 123, 10200; Correction: J. Am. Chem. Soc. 2002, 124, 7249.
25. Kleinbeck, F.; Carreira, E. M. Angew. Chem. Int. Ed. 2009, 48, 578.
26. Quéron, E.; Lett, R. Tetrahedron Lett. 2004, 45, 4539; and references cited therein.
27. Marshall, J. A.; Adams, N. D. J. Org. Chem. 2002, 67, 733.
28. (a) Poupon, J.-C.; Demont, E.; Prunet, J.; Férézou, J.-P. J. Org. Chem. 2003, 68, 4700.
29. (b) Lopez, R.; Poupon, J.-C.; Prunet, J.; Férézou, J.-P.; Ricard, L. Synthesis 2005, 644.
30. Yadav, J. S.; Reddy, K. B.; Sabitha, G. Tetrahedron 2008, 64, 1971.
31. Paterson, I.; Bower, S.; McLeod, M. D. Tetrahedron Lett. 1995, 36, 175.
32. Eustache, F.; Dalko, P. I.; Cossy, J. J. Org. Chem. 2003, 68, 9994.
33. For reviews on the total synthesis of plecomacrolides, see: Toshima, K. Curr. Org. Chem. 2004, 8, 185; and ref. 3.
34. For selected reviews on RCM, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
35. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
36. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
37. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
38. (e) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
39. (f) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490.
40. (g) Gradillas, A.; Pérez-Castells, J. Angew. Chem. Int. Ed. 2006, 45, 6086.
41. (h) Schrodi, Y.; Pederson, R. L. Aldrichimica Acta 2007, 40, 45.
42. (i) Hoveyda, A. H.; Zhugralin, A. R. Nature 2007, 450, 243.
43. (j) Handbook of Metathesis, Vol.1-3; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
44. For selected examples of 1,3-diene-ene RCM in the synthesis of macrocycles, see: (a) Hayashi, Y.; Shoji, M.; Ishikawa, H.; Yamaguchi, J.; Tamura, T.; Imai, H.; Nishigaya, Y.; Takabe, K.; Kakeya, H.; Osada, H. Angew. Chem. Int. Ed. 2008, 47, 6657.
45. (b) Wang, L.; Gong, J.; Deng, L.; Xiang, Z.; Chen, Z.; Wang, Y.; Chen, J.; Yang, Z. Org. Lett. 2009, 11, 1809; see also the early references cited in ref. 26.
46. For our recent work on the use of RCM in total synthesis, see: (a) Jin, J.; Chen, Y.; Li, Y.; Wu, J.; Dai, W.-M. Org. Lett. 2007, 9, 2585.
47. (b) Dai, W.-M.; Chen, Y.; Jin, J.; Wu, J.; Lou, J.; He, Q. Synlett 2008, 1737.
48. (c) Dai, W.-M.; Shi, L.; Li, Y. Tetrahedron: Asymmetry 2008, 19, 1549.
49. Lu, K.; Huang, M.; Xiang, Z.; Liu, Y.; Chen, J.; Yang, Z. Org. Lett. 2006, 8, 1193.
50. Guan, Y.; Wu, J.; Sun, L.; Dai, W.-M. J. Org. Chem. 2007, 72, 4953.
51. -3 mmol) followed by stirring at 80°C for 4 h. After cooling to r.t., the reaction mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel; EtOAc-hexane, 2%) to provide the RCM product. For the RCM reaction of 21 (Scheme 4), the loading of 8 was 13 mol% and the reaction time was 11 h instead of 4 h.
52. +: 597.3376; found: 597.3352.
53. +: 611.3527; found: 611.3533.
54. +: 639.3476; found: 639.3468.
55. Dai, W.-M.; Feng, G.; Wu, J.; Sun, L. Synlett 2008, 1013.
56. (a) Andrus, M. B.; Soma Sekhar, B. B. V.; Turner, T. M.; Meredith, E. L. Tetrahedron Lett. 2001, 42, 7179.
57. (b) Andrus, M. B.; Meredith, E. L.; Simmons, B. L.; Soma Sekhar, B. B. V.; Hicken, E. J. Org. Lett. 2002, 4, 3549.
58. 6: 422.2668; found: 422.2662.
59. 1H NMR spectrum of the reaction mixture.
60. Granberg, K. L.; Edvinsson, K. M.; Nilsson, K. Tetrahedron Lett. 1999, 40, 755.