Syntheses of CP-225,917 and CP-263,114

Angewandte Chemie - International Edition

Volumn 39, Issue 8, 2000, Pages 1415-1421

  Starr, Jeremy T ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Epimerizations; Natural products; Polycycles; Synthetic methods; Total synthesis

Indexed keywords

CP 225017; CP 225917; CP 263114; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; DRUG INDUSTRY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0034678605     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122.
2. K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. 2000, 112, 46-126; Angew. Chem. Int. Ed. 2000, 39, 44-122.
3. a) T. T. Dabrah, T. Kaneko, W. Massefski, Jr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594;
4. b) T. T. Dabrah, H. J. Harwood, Jr., L. H. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, J. Antibiot. 1997, 50, 1;
5. c) The syntheses of CP-263,114 and CP-225,917 were recently reviewed. see: Nach. Chem. Lab. Tech. 1999, 47, 1423.
6. a) S. A. Biller, K. Neuenschwander, M. M. Ponpipom, C. D. Poulter, Curr. Pharm. Des. 1996, 2, 1;
7. b) D. M. Leonard, J. Med. Chem. 1997, 40, 2971.
8. The total synthesis of several members of this class of natural products have been reported, see: a) E. M. Carreira, J. Du Bois, J. Am. Chem. Soc. 1994, 116, 10825;
9. b) E. M. Carreira, J. Du Bois, J. Am. Chem. Soc. 1995, 117, 8106;
10. c) K. C. Nicolaou, E. W. Yue, N. Yoshimitsu, F. De Riccardis, A. Nadin, J. E. Leresche, S. La Greca, Z. Yang, Angew. Chem. 1994, 106, 2306; Angew. Chem. Int. Ed. Engl. 1994, 33, 2184;
11. c) K. C. Nicolaou, E. W. Yue, N. Yoshimitsu, F. De Riccardis, A. Nadin, J. E. Leresche, S. La Greca, Z. Yang, Angew. Chem. 1994, 106, 2306; Angew. Chem. Int. Ed. Engl. 1994, 33, 2184;
12. d) K. C. Nicolaou, A. Nadin, J. E. Leresche, S. La Greca, T. Tsuri, E. W. Yue, Z. Yang, Angew. Chem. 1994, 106, 2309; Angew. Chem. Int. Ed. Engl. 1994, 33, 2187;
13. d) K. C. Nicolaou, A. Nadin, J. E. Leresche, S. La Greca, T. Tsuri, E. W. Yue, Z. Yang, Angew. Chem. 1994, 106, 2309; Angew. Chem. Int. Ed. Engl. 1994, 33, 2187;
14. e) K. C. Nicolaou, A. Nadin, J. E. Leresche, E. W. Yue, S. La Greca, Angew. Chem. 1994, 106, 2312; Angew. Chem. Int. Ed. Engl. 1994, 33, 2190;
15. e) K. C. Nicolaou, A. Nadin, J. E. Leresche, E. W. Yue, S. La Greca, Angew. Chem. 1994, 106, 2312; Angew. Chem. Int. Ed. Engl. 1994, 33, 2190;
16. f) Zaragozic acid C, see: D. A. Evans, J. C. Barrow, J. L. Leighton, A. J. Robichaud, M. Sefkow, J. Am. Chem. Soc. 1994, 116, 12111;
17. g) S. Caron, D. Stoermer, A. K. Mapp, C. H. Heathcock, J. Org. Chem. 1996, 61, 9126;
18. h) D. Stoermer, S. Caron, C. H. Heathcock, J. Org. Chem. 1996, 61, 9115;
19. H. Sato, S. Nakamura, N. Watanabe, S. Hashimoto, Synlett 1997, 451;
20. j) K. C. Nicolaou, E. W. Yue, S. La Greca, A. Nadin, Z. Yang, J. E. Leresche, T. Tsuri, Y. Naniwa, F. De Riccardis, Chem. Eur. J. 1995, 1, 467;
21. k) A. Armstrong, L. H. Jones, P. A. Barsanti, Tetrahedron Lett. 1998, 39, 3337.
22. A. Armstrong, T. J. Critchley, A. A. Mortlock, Synlett 1998, 552.
23. P. W. M. Sgarbi, D. L. J. Clive, Chem. Commun. 1997, 2157.
24. a) D. Meng, O. Tan, S. J. Danishefsky, Angew. Chem. 1999, 111, 3393; Angew. Chem. Int. Ed. 1999, 38, 3197;
25. a) D. Meng, O. Tan, S. J. Danishefsky, Angew. Chem. 1999, 111, 3393; Angew. Chem. Int. Ed. 1999, 38, 3197;
26. b) D. Meng, S. J. Danishefsky, Angew. Chem. 1999, 111, 1582; Angew. Chem. Int. Ed. 1999, 38, 1485;
27. b) D. Meng, S. J. Danishefsky, Angew. Chem. 1999, 111, 1582; Angew. Chem. Int. Ed. 1999, 38, 1485;
28. c) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky, Angew. Chem. 1998, 110, 1981; Angew. Chem. Int. Ed. 1998, 37, 1880;
29. c) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky, Angew. Chem. 1998, 110, 1981; Angew. Chem. Int. Ed. 1998, 37, 1880;
30. d) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky, Angew. Chem. 1998, 110, 1978; Angew. Chem. Int. Ed. 1998, 37, 1877.
31. d) O. Kwon, D.-S. Su, D. Meng, W. Deng, D. C. D'Amico, S. J. Danishefsky, Angew. Chem. 1998, 110, 1978; Angew. Chem. Int. Ed. 1998, 37, 1877.
32. N. Waizumi, T. Itoh, T. Fukuyama, Tetrahedron Lett. 1998, 39, 6015.
33. M. M. Bio, J. L. Leighton, J. Am. Chem. Soc. 1999, 121, 190.
34. a) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669;
35. a) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, W. H. Yoon, Y. He, K. C. Fong, Angew. Chem. 1999, 111, 1774; Angew. Chem. Int. Ed. 1999, 38, 1669;
36. b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781; Angew. Chem. Int. Ed. 1999, 38, 1676;
37. b) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, K. C. Fong, Y. He, W. H. Yoon, H.-S. Choi, Angew. Chem. 1999, 111, 1781; Angew. Chem. Int. Ed. 1999, 38, 1676;
38. c) K. C. Nicolaou, Y. He, K. C. Fong, W. H. Yoon, H.-S. Choi, Y.-L. Zhong, P. S. Baran, Org. Lett. 1999, 1, 63;
39. d) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, H.-S. Choi, K. C. Fong, Y. He, W. H. Yoon, Org. Lett. 1999, 1, 883.
40. C. Chen, M. E. Layton, M. D. Shair, J. Am. Chem. Soc. 1998, 120, 10784.
41. H. W. Thompson, J. K. Wong, R. A. Lalancette, J. A. Boyko, A. M. Robertiello, J. Org. Chem. 1985, 50, 2115.
42. Editor's note: An asymmetric total synthesis of the CP compounds has just been completed: K. C. Nicolaou, J.-K. Jung, W. H. Yoon, Y. He, Y.-L. Zhong, P. S. Baran, Angew. Chem., in press.