A highly stereoselective total synthesis of hispidospermidin: Derivation of a pharmacophore model

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6151-6159

  Frontier, Alison J ^a,c   Raghavan, Subharekha ^a,d   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^c STANFORD UNIVERSITY   (United States)

^d MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HISPIDOSPERMIDIN; KETONE; NATURAL PRODUCT; SPERMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; CYTOTOXICITY; DERIVATIZATION; HYDROPHOBICITY; MODEL; PHARMACOPHORE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0034608840     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9944960     Document Type: Article

References (30)

1. (a) Yanagisawa, M.; Sakai, A.; Adachi, K.; Sano, T.; Watanabe, K.; Tanaka, Y.; Okuda, T. J. Antibiot. 1994, 47, 1.
2. (b) Ohtsuka, T.; Itezono, Y.; Nakayama, N.; Sakai, A.; Shimma, N.; Yokose, K.; Seto, H. J. Antibiot. 1994, 47, 6.
3. (a) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933.
4. (b) Magerus, P. W.; Connolly, T. M.; Deckmyn, H.; Ross, T. S.; Bross, T. E.; Ishii, H.; Bansal, V. S.; Wilson, D. B. Science 1986, 234, 1519.
5. Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315.
6. For a preliminary communication, see: Frontier, A. J.; Raghavan, S.; Danishfsky, S. J. J. Am. Chem. Soc. 1997, 119, 6686.
7. For a thorough treatment of this work, see: Frontier, A. J. Ph.D. Thesis, Columbia University, 1999.
8. For an asymmetric synthesis of hispidospermidin, see: Overman, L. E.; Tomasi, A. L. J. Am. Chem. Soc. 1998, 120, 4039.
9. Carbon numbering anticipates the hispidospermidin numbering system introduced in ref 1.
10. (a) Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152.
11. (b) Boeckmann, R. K., Jr.; Blum, D. M.; Ganem, B.; Halvey, N. Org. Synth. Collect. Vol. VI 1988, 1033.
12. Büchi, G.; Wüest, H. J. Org. Chem. 1969, 34, 1122.
13. Bierer, D. E.; Kabalka, G. W. Org. Prep. Proc. Int. 1988, 20, 63.
14. Stork, G.; Ozorio, A. A.; Leong, A. Y. W. Tetrahedron Lett. 1978, 5175.
15. Boeckmann, R. K., Jr.; Blum, D. M.; Ganem, B. Org. Synth. Collect. Vol. VI 1988, 666 and references therein.
16. Drouin, J. D.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
17. (a) Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 2773.
18. (b) Huang, H.; Forsyth, C. J. J. Org. Chem. 1995, 60, 5746.
19. (a) Stork, G.; Darling, S. D. J. Am. Chem. Soc. 1960, 82, 1513.
20. (b) Stork, G.; Darling, S. D. J. Am. Chem. Soc. 1964, 86, 1761.
21. Caine, D. Org. React. (N. Y.) 1976, 23, 1.
22. Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1978, 43, 1599.
23. Kawada, K.; Gross, R. S.; Watt, D. S. Synth. Commun. 1989, 5&6, 777.
24. Hamilton, R.; Walker, B. J.; Walker, B. Tetrahedron Lett. 1993, 34, 2847.
25. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673.
26. Stevens, R. V.; Beaulieu, N.; Chan, W. H.; Daniewski, A. R.; Takeda, T.; Waldner, A.; Williard, P. G.; Zutter, U. J. Am. Chem. Soc. 1986, 108, 1039.
27. Ford, H.; Chang, C.-H.; Behrman, E. J. J. Am. Chem. Soc. 1981, 103, 7773.
28. Wenkert, E.; Golob, N. F.; Sathe, S. S.; Smith, R. A. J. Synth. Commun. 1973, 205 and references therein.
29. Campbell, A. S.; Thatcher, G. R. J. Tetrahedron Lett. 1991, 32, 2207.
30. Ryan, M.; Smith, M. P.; Vinod, T. K.; Lau, W. L.; Keana, J. F. W.; Griffith, O. H. J. Med. Chem. 1996, 39, 4366.