Late-stage intermolecular CH activation for lead diversification: A highly chemoselective oxyfunctionalization of the C-9 position of potent bryostatin analogues

Organic Letters

Volumn 7, Issue 1, 2005, Pages 79-82

  Wender, Paul A ^a   Hilinski, Michael K ^a   Mayweg, Alexander V W ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRYOSTATIN; BRYOSTATIN 1; BRYOSTATIN 2; BRYOSTATIN DERIVATIVE; CARBON; DIMETHYLDIOXIRANE; HYDROGEN; HYDROXYL GROUP; LEAD; OXYGEN; UNCLASSIFIED DRUG; MACROLIDE; PROTEIN KINASE C;

ACYLATION; ARTICLE; CHEMICAL BOND; DRUG POTENCY; HYDROXYLATION; OXIDATION; SUBSTITUTION REACTION; CHEMISTRY; HYDROGEN BOND; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROGEN BONDING; HYDROXYLATION; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN KINASE C;

EID: 12344263136     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047859w     Document Type: Article

References (47)

1. West, C. A. In The Biochemistry of Plants; Davis, D. D., Ed.; Academic Press: New York, 1980; Vol. 2.
2. Hefner, J.; Rubenstein, S. M.; Ketchum, R. E. B.; Gibson, D. M.; Williams, R. M.; Croteau, R. Chem. Biol. 1996, 3, 479-489.
3. For recent reviews, see: (a) Davies, H. M. L.; Beckwith, R. E. J. Chem Rev. 2003, 103, 2861-2903. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101. (c) Ritleng, V.; Sirlin, C. Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
4. For recent reviews, see: (a) Davies, H. M. L.; Beckwith, R. E. J. Chem Rev. 2003, 103, 2861-2903. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101. (c) Ritleng, V.; Sirlin, C. Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
5. For recent reviews, see: (a) Davies, H. M. L.; Beckwith, R. E. J. Chem Rev. 2003, 103, 2861-2903. (b) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101. (c) Ritleng, V.; Sirlin, C. Pfeffer, M. Chem. Rev. 2002, 102, 1731-1770.
6. Yang, J.; Gabriele, B.; Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057-5067 and references therein.
7. For impressive recent examples, see: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511. (b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857. (d) Taber, D. F.; Storck, P. H. J. Org. Chem. 2003, 68, 7768-7771. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871-7884.
8. For impressive recent examples, see: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511. (b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857. (d) Taber, D. F.; Storck, P. H. J. Org. Chem. 2003, 68, 7768-7771. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871-7884.
9. For impressive recent examples, see: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511. (b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857. (d) Taber, D. F.; Storck, P. H. J. Org. Chem. 2003, 68, 7768-7771. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871-7884.
10. For impressive recent examples, see: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511. (b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857. (d) Taber, D. F.; Storck, P. H. J. Org. Chem. 2003, 68, 7768-7771. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871-7884.
11. For impressive recent examples, see: (a) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510-11511. (b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707. (c) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856-11857. (d) Taber, D. F.; Storck, P. H. J. Org. Chem. 2003, 68, 7768-7771. (e) White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64, 7871-7884.
12. (a) Lee, S.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 13978-13979.
13. (b) Lee, J. S., Fuchs, P. L. Org. Lett. 2003, 5, 2247-2250.
14. (c) Breslow, R.; Zhang, X.; Huang, Y. J. Am. Chem. Soc. 1997, 119, 4535-4536.
15. (d) Chen, M. S.; White, M. C. J. Am. Chem. Soc. 2004, 126, 1346-1347.
16. (e) Dick, A. R.; Hull, K. L.: Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301.
17. (f) Desai, L. V.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 9542-9543.
18. (a) Mutter, R.; Wills, M. Bioorg. Med. Chem. 2000, 8, 1841-1860.
19. (b) Pettit, G. R. J. Nat. Prod. 1996, 59, 812-821.
20. (c) Hale, K. J.; Hummersone, M. G.; Manaviazar, S.; Frigerio, M. Nat. Prod. Rep. 2002, 19, 413-453.
21. For current information, see: http://clinicaltrials.gov
22. Wender, P. A.; Baryza, J. L.; Bennett, C. E.; Bi, F. C.; Brenner, S. E.; Clarke, M. O.; Horan, J. C.; Kan, C.; LaCote, E.; Lippa, B. S.; Nell, P. G.; Turner, T. M. J. Am. Chem. Soc. 2002, 124, 13648-13649.
23. (a) Wender, P. A.; De Brabander J.; Harran, P. G.; Jiminez, J.-M.; Koehler, M. F. T.; Lippa, B.; Park, C.-M.; Shiozaki, M. J. Am. Chem. Soc. 1998, 120, 4534-4535.
24. (b) Wender, P. A.; Hinkle, K. W.; Koehler, M. F. T.; Lippa, B. Med. Res. Rev. 1999, 19, 388-407.
25. (c) Wender, P. A.; MartinCantalejo, Y.; Carpenter, A. J.; Chiu, A.; DeBrabander, J.; Harran, P. G.; Jiminez, J. M.; Koehler, M. F. T.; Lippa, B.; Morrison, J. A.; Muller, S. G.; Muller, S. N.; Park, C.-M.; Shiozaki, M.; Siedenbiedel, C.; Skalitzky, D. J.; Tanaka, M.; Irie, K. Pure Appl. Chem. 1998, 70, 539-546.
26. Wender, P. A.; DeBrabander, J.; Harran, P. G.; Jimenez, J.-M.; Koehler, M. F. T.; Lippa, B.; Park, C.-M.; Siedenbiedel, C.; Pettit, G. R. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 6624-6629.
27. Adam, W.; Edwards, J. O.; Curci, R. Acc. Chem. Res. 1989, 22, 205-211.
28. Baumstark, A. L.; Vasquez, P. C. J. Org. Chem. 1988, 53, 3437-3439.
29. (a) Buxton, C. P.; Marples, B. A.; Toon, R. C.; Waddington, V. L. Tetrahedron Lett. 1999, 40, 4729-4732.
30. (b) Bovicelli, P.; Lupattelli, P.; Sanetti, A. Tetrahedron Lett. 1994, 35, 8477-8480.
31. (a) Bovicelli, P.; Lupattelli, P.; Fiorini, V. Tetrahedron Lett. 1993, 34, 6103-6104.
32. (b) Horiguchi, T.; Cheng, Q.; Oritani, T. Tetrahedron Lett. 2000, 41, 3907-3910.
33. (a) Curci, R.; D-Accolti, L.; Fiorentino, M.; Fusco, C.; Adam, W.; González-Nuñez, M. E.; Mello, R. Tetrahedron Lett. 1992, 33, 4225-4228.
34. (b) Van Heerden, F. R.; Dixon, J. T.; Holzapfel, C. W. Tetrahedron Lett. 1992, 33, 7399-7402.
35. Adam, W.; Bialas, J.; Hadjiarapoglou, I. Chem. Ber. 1991, 124, 2377.
36. (a) Curci, R.; D-Accolti, L.; Fusco, C. Tetrahedron Lett. 2001, 42, 7087-7090.
37. (b) Newcomb, M.; Choi, S.-Y.; Simakov, P. A. Tetrahedron Lett. 1998, 39, 8187-8190.
38. (c) Glukhovtsev, M. N.; Canepa, C.; Bach, R. D. J. Am. Chem. Soc. 1998, 120, 10528-10533.
39. (c) Houk, K. N.; Du, X. J. J. Org. Chem. 1998, 63, 6480-6483.
40. Mello, R.; Cassidei, L.; Fiorentino, M.; Fusco, C.; Hümmer, W.; Jäger, V.; Curci, R. J. Am. Chem. Soc. 1991, 113, 2204-2208.
41. Baumstark, A. L.; Kovac, F.; Vasquez, P. C. Can. J. Chem. 1999, 77, 308-312.
42. (a) Mutter, R.; Willis, M. Bioorg. Med. Chem. 2000, 8, 1841-1860.
43. (b) Pettitt, G. R. J. Nat. Prod. 1996, 59, 812-821.
44. For representative examples of hemiketal-containing natural products, see: apoptolidin, callipeltoside, the cephalostatins, and the phorboxazoles. (a) Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.-i.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525. (b) Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088. (c) Pettit, G. R.; Tan, R.; Xu, J.-P.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 955-958 and references therein. (d) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131.
45. For representative examples of hemiketal-containing natural products, see: apoptolidin, callipeltoside, the cephalostatins, and the phorboxazoles. (a) Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.-i.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525. (b) Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088. (c) Pettit, G. R.; Tan, R.; Xu, J.-P.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 955-958 and references therein. (d) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131.
46. For representative examples of hemiketal-containing natural products, see: apoptolidin, callipeltoside, the cephalostatins, and the phorboxazoles. (a) Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.-i.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525. (b) Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088. (c) Pettit, G. R.; Tan, R.; Xu, J.-P.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 955-958 and references therein. (d) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131.
47. For representative examples of hemiketal-containing natural products, see: apoptolidin, callipeltoside, the cephalostatins, and the phorboxazoles. (a) Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.-i.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525. (b) Zampella, A.; D'Auria, M. V.; Minale, L.; Debitus, C.; Roussakis, C. J. Am. Chem. Soc. 1996, 118, 11085-11088. (c) Pettit, G. R.; Tan, R.; Xu, J.-P.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 955-958 and references therein. (d) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126-8131.