Synthetic studies toward the bryostatins: A substrate-controlled approach to the A-ring

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3667-3670

  Keck, Gary E ^a   Welch, Dennie S ^a   Vivian, Paige K ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRYOSTATIN; BRYOSTATIN 1; MACROLIDE;

ANIMAL; ARTICLE; BRYOZOA; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANIMALS; BRYOSTATINS; BRYOZOA; MACROLIDES; MOLECULAR STRUCTURE;

EID: 33748690321     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061173h     Document Type: Article

References (41)

1. Pettit, G. R.; C. L.; Douobek, D. L.; Herald, D. L. J. Am. Chem. Soc. 1982, 104, 6846.
2. For reviews, see: (a) Hale, K. J.; Hummersome, M. G.; Manaviazar, S.; Frigerio, M. Nat. Prod. Rep. 2002, 19, 413.
3. (b) Mutter, R.; Wills, M. Bioorg. Med. Chem. 2000, 8, 1841.
4. Al-Katib, A. M.; Smith, M. R.; Kamanda, W. S.; Pettit, G. R.; Hamdan, M.; Mohamed, A. N.; Chelladurai, B.; Mohammad, R. M. Clin. Cancer Res. 1998, 4, 1305.
5. Etcheberrigaray, R.; Tan, M.; Dewachter, I.; Kuiperi, C.; Van der Auwera, I.; Wera, S.; Qiao, L.; Bank, B.; Nelson, T. J.; Kozikowski, A. P.; Van Leuven, F.; Alkon, D. L. Proc. Natl. Acad. Sci., U.S.A. 2004, 101, 1141.
6. Dell'Aquila, M. L.; Herald, C. L.; Kamano, Y.; Pettit, G. R.; Blumberg, P. M. Cancer Res. 1988, 48, 3702.
7. Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407.
8. Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540.
9. Ohmori, K.; Ogawa, Y.; Obitsu, T.; Ishikawa, Y.; Nishiyama, S.; Yamamura, S. Angew. Chem., Int. Ed. 2000, 39, 2290.
10. For recent synthetic work in this area, see: (a) Voight, E. A.; Seradj, H.; Roethle, P. A.; Burke, S. D. Org. Lett. 2004, 6, 4045.
11. (b) Voight, E. A.; Roethle, P. A.; Burke, S. D. Org. Lett. 2004, 6, 4534.
12. (c) Hale, K. J.; Frigerio, M.; Manaviazar, S.; Hummersome, M. G.; Fillingham, I. J.; Barsukov, I. G.; Damblon, C. F.; Gerscher, A.; Roberts, G. C. K. Org. Lett. 2003, 5, 499.
13. (d) Hale, K. J.; Frigerio, M.; Hummersome, M. G.; Manaviazar, S. Org. Lett. 2003, 5, 503.
14. (e) Ball, M.; Baron, A.; Bradshaw, B.; Omori, H.; MacCormick, S.; Thomas, E. J. Tetrahedron Lett. 2004, 45, 8747.
15. (f) Keck, G. E.; Yu, T.; McLaws, M. D. J. Org. Chem. 2005, 70, 2543.
16. (g) Keck, G. E.; Truong, A. P. Org. Lett. 2005, 7, 2149.
17. (h) Keck, G. E.; Truong, A. P. Org. Lett. 2005, 7, 2153.
18. (i) Ball, M.; Bradshaw, B. J.; Dumeunier, R.; Gregson, T. J.; MacCormick, S.; Omori, H.; Thomas, E. J. Tetrahedron Lett. 2006, 47, 2223.
19. See, tor example: (a) Stone, J. C.; Stang, S. L.; Zheng, Y.; Dower, N. A.; Brenner, S. E.; Baryza, J. L.; Wender, P. A. J. Med. Chem. 2004, 47, 6638.
20. (b) Wender, P. A.; Baryza, J. L.; Brenner, S. E.; Clarke, M. O.; Craske, M. L.; Horan, J. C.; Meyer, T. Curr. Drug Discuss. Tech. 2004, 1, 1.
21. (c) Wender, P. A.; Mayweg, A. V. W.; VanDeusen, C. L. Org. Lett. 2003, 5, 277.
22. (d) Wender, P. A.; Baryza, J.; Bennett, C.; Bi, C.; Brenner, S. E.; Clarke, M.; Horan, J.; Kan, C.; Lacote, E.; Lippa, B.; Nell, P.; Turner, T. J. Am. Chem. Soc. 2002, 124, 13648.
23. Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189.
24. (a) Bunnelle, W. H.; Narayanan, B. A. Tetrahedron Lett. 1987, 28, 6261.
25. (b) Bunnelle, W. H.; Narayanan, B. A. Org. Synth. 1990, 8, 89.
26. (a) Keck, G. E.; Castellino, S.; Wiley, M. R. J. Org. Chem. 1986, 51, 5478.
27. (b) Evans, D. A.; Duffy, J. L.; Dart, M. J. Tetrahedron Lett. 1994, 35, 8537.
28. (c) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462 and references therein.
29. Yadav, J. S.; Bandyopadhyay, A.; Kunwar, A. C. Tetrahedron Lett. 2001, 42, 4907.
30. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
31. (b) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 75, 12.
32. Ramachandran, P.; Krzeminksi, M. P.; Reddy, R. V.; Brown, H. C. Tetrahedron: Asymmetry 1999, 10, 11.
33. Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180.
34. For a similar synthetic sequence involving introduction of a 1,1-dimethyl unsaturated olefin, see: Hirai, K.; Ooi, H.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 857.
35. Weigand, S.; Brückner, R. Synthesis 1996, 475.
36. For a related chelation-controlled Mukaiyama addition involving a PMB-protected β-hydroxy aldehyde, see ref 7.
37. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
38. 4 followed by filtration and removal of benzene under reduced pressure afforded the aldehyde which could be carried onto the coupling without the need for further manipulation. The origin of the difference in stability to chromatography between aldehydes 18 and 19 is unclear at present.
39. Evans, D. A.; Allison, B. A.; Yang, M. G.; Masse, C. E. J. Am. Chem. Soc. 2001, 123, 10840.
40. 2AlCl (TBDPS ethers do not) and therefore could be a source of chelate disruption, leading to lower diastereoselectivity than that observed with the TBDPS-containing aldehydes. See ref 23.
41. Bal, B. S.; Childers, W. E.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.