Synthesis of the C11-C29 fragment of amphidinolide F

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3865-3868

  Shotwell, J Brad ^a   Roush, William R ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE F; ANTINEOPLASTIC AGENT; UNCLASSIFIED DRUG;

ALDOL REACTION; ANNULATION REACTION; ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; METASTASIS INHIBITION; STEREOCHEMISTRY;

HETEROCYCLIC COMPOUNDS; MACROLIDES;

EID: 7044233499     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048381z     Document Type: Article

References (53)

1. For recent reviews, see: (a) Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753. (b) Chakraborty, T.; Das, S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131. (c) Kobayashi, J.; Shimbo, K.; Kubota, T.; Tsuda, M. Pure Appl. Chem. 2003, 75, 337. (d) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
2. For recent reviews, see: (a) Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753. (b) Chakraborty, T.; Das, S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131. (c) Kobayashi, J.; Shimbo, K.; Kubota, T.; Tsuda, M. Pure Appl. Chem. 2003, 75, 337. (d) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
3. For recent reviews, see: (a) Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753. (b) Chakraborty, T.; Das, S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131. (c) Kobayashi, J.; Shimbo, K.; Kubota, T.; Tsuda, M. Pure Appl. Chem. 2003, 75, 337. (d) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
4. For recent reviews, see: (a) Kobayashi, J.; Ishibashi, M. Chem. Rev. 1993, 93, 1753. (b) Chakraborty, T.; Das, S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131. (c) Kobayashi, J.; Shimbo, K.; Kubota, T.; Tsuda, M. Pure Appl. Chem. 2003, 75, 337. (d) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
5. (a) Pattenden, G.; Lam, H. Angew. Chem., Int. Ed. 2002, 41, 508.
6. (b) Maleczka, R.; Terrell, L.; Geng, F.; Ward, J. Org. Lett. 2002, 4, 2841.
7. Trost, B.; Chisholm, J.; Wrobleski, S.; Jung, M. J. Am. Chem. Soc. 2002, 124, 12420.
8. Trost, B.; Harrington, P. J. Am. Chem. Soc. 2003, 726, 5028.
9. Williams, D.; Meyer, K. J. Am. Chem. Soc. 2001, 123, 765.
10. Williams, D.; Myers, B.; Mi, L. Org. Lett. 2000, 2, 945.
11. Williams, D.; Kissel, W. J. Am. Chem. Soc. 1998, 120, 11198.
12. Kissel, W. Ph.D. Dissertation, Indiana University, Bloomington, IN, 1998.
13. (a) Fürstner, A.; Aissa, C.; Riveiros, R.; Ragot, J. Angew. Chem., Int. Ed. 2002, 41, 4763.
14. (b) Ghosh, A.; Liu, C. J. Am. Chem. Soc. 2003, 725, 2374.
15. Aiessa, C.; Riveiros, R.; Ragot, J.; Fürstner, A. J. Am. Chem. Soc. 2003, 125, 15512.
16. Colby, E.; O'Brien, K.; Jamison, T. J. Am. Chem. Soc. 2004, 126, 998.
17. Ghosh, A.; Gong, G. J. Am. Chem. Soc. 2004, 126, 3704.
18. Kobayashi, J.; Tsuda, M.; Ishibashi, M.; Shigemori, H.; Yamasu, T.; Hirota, H.; Sasaki, T. J. Antibiot. 1991, 44, 1259.
19. Kobayashi, J.; Ishibashi, M.; Wälchli, M.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Ohizumi, Y. J. Am. Chem. Soc. 1988, 110, 490.
20. (a) Ishiyama, H.; Ishibashi, M.; Kobayashi, J. Chem. Pharm. Bull. 1996, 44, 1819.
21. (b) Kubota, T.; Tsuda, M.; Kobayashi, J. Org. Lett. 2001, 3, 1363.
22. Kubota, T.; Tsuda, M.; Kobayashi, J. Tetrahedron 2003, 59, 1613.
23. (a) Panek, J.; Yang, M. J. Am. Chem. Soc. 1991, 113, 9868.
24. (b) Panek, J.; Beresis, R. J. Org. Chem. 1993, 58, 809.
25. Micalizio, G.; Roush, W. Org. Lett. 2000, 2, 461.
26. (a) Davies, H.; Hansen, T.; Rutberg, J.; Bruzinski, P. Tetrahedron Lett. 1997, 38, 1741.
27. (b) Bulugahapitiya, P.; Landais, Y.; Parra-Rapado, L.; Planchenault, D.; Weber, V. J. Org. Chem. 1997, 62, 1630.
28. (a) Paterson, I.; Goodman, J.; Isaka, M. Tetrahedron Lett. 1989, 30, 7121.
29. (b) Gustin, D. J.; VanNieuwenhze, M. S.; Roush, W. R. Tetrahedron Lett. 1995, 36, 3443.
30. Roush, W. R.; Dilley, D. J. Tetrahedron Lett. 1999, 40, 4955.
31. Evans, D.; Hoveyda, A. J. Am. Chem. Soc. 1990, 112, 6447.
32. Nicolaou, K.; Murphy, F.; Barluenga, S.; Ohshima, T.; Wei, H.; Xu, J.; Gray, D.; Baudoin, O. J. Am. Chem. Soc. 2000, 122, 3830.
33. Roush, W.; Pinchuk, A.; Micalizio, G. Tetrahedron Lett. 2000, 41, 9413.
34. Stereochemistry of 15 was assigned by NOE studies of the derived alcohol 16 and chemical correlation with a known compound (see Supporting Information).
35. Greene, T.; Wuts, P. Protective Groups in Organic Synthesis; Wiley & Sons: New York, 1999.
36. Derived in one step from known iodide 18: Walkup, R.; Boatman, D.; Kane, R.; Cunningham, R. Tetrahedron Lett. 1991, 32, 3937.
37. Micalizio, G.; Roush, W. Org. Lett. 2001, 3, 1949.
38. (a) Hudrlik, P.; Hudrlik, A.; Kulkarni, A. J. Am. Chem. Soc. 1982, 104, 6809.
39. (b) Hudrlik, P.; Holmes, P.; Hudrlik A. Tetrahedron Lett. 1988, 29, 6395.
40. Hudrlik, P.; Gebreselassie, P.; Tafesse, L.; Hudrlik, A. Tetrahedron Lett. 2003, 44, 3409.
41. 2Ph bond cleavage, see: Anderson, J.; Flaherty, A. J. Chem. Soc., Perkin Trans. 1 2000, 3025.
42. 2Ph bond cleavage, see: Anderson, J.; Flaherty, A. J. Chem. Soc., Perkin Trans. 1 2000, 3025.
43. Hale, M.; Hoveyda, A. J. Org. Chem. 1992, 57, 1643.
44. Subsequent experimentation has revealed that the adjacent hydroxyl group is not required for efficient protiodesilylation in related systems, suggesting that siloxane intermediates may not be involved in this case. The present process seems to be fluoride mediated (entry 5, Table 1), in contrast to similar transformations reported by Hudrlik. Further optimization/ study of this transformation will be reported in due course.
45. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
46. Parikh, J.; Doering, W. J. Am. Chem. Soc. 1967, 89, 5505.
47. Smith, A.; Doughty, V.; Sfouggatakis, C.; Bennett, C.; Koyanagi, J.; Takeuchi, M. Org. Lett. 2002, 4, 783.
48. (a) Dale, J.; Mosher, H. J. Am. Chem. Soc. 1973, 95, 512.
49. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
50. Hydrolysis of the benzoate ester and formation of the corresponding acetonide indicated that the C(13,15) diol has anti stereochemistry: Rychnovsky, S.; Rogers, B.; Richardson, T. Acc. Chem. Res. 1998, 31, 9.
51. Zhang, H.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
52. Farina, V.; Krishnamurthy, V.; Scott, W. Org. React. 1997, 50, 1.
53. Saihi, M.; Pereyre, M. Bull. Soc. Chim. Fr. 1977, 1251.