Total synthesis of dictyodendrin B

Journal of the American Chemical Society

Volumn 127, Issue 33, 2005, Pages 11620-11621

  Fürstner, Alois ^a   Domostoj, Mathias M ^a   Scheiper, Bodo ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; DICTYODENDRIN B; UNCLASSIFIED DRUG;

ALKYLATION; AROMATIZATION; ARTICLE; BROMINATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; OXIDATION;

ACETOPHENONES; ANIMALS; CARBAZOLES; MOLECULAR STRUCTURE; PORIFERA; PYRROLES;

EID: 23944462404     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0541175     Document Type: Article

References (31)

1. (a) Kim, N. W.; Piatyszek, M. A.; Prowse, K. R.; Harley, C. B.; West, M. D.; Ho, P. L. C.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J. W. Science 1994, 266, 2011.
2. (b) Herbert, B.-S.; Pitts, A. E.; Baker, S. I.; Hamilton, S. E.; Wright, W. E.; Shay, J. W.; Corey, D. R. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 14276.
3. Reviews: (a) Neidle, S.; Parkinson, G. Nat. Rev. Drug Discovery 2002, 1, 383.
4. (b) Neidle, S.; Thurston, D. E. Nat. Rev. Cancer 2005, 5, 285.
5. Telomestatin is the most prominent naturally occurring telomerase inhibitor. See: Shin-ya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262.
6. Warabi, K.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 2003, 68, 2765.
7. Sato, A.; Morishita, T.; Shiraki, T.; Yoshioka, S.; Horikoshi, H.; Kuwano, H.; Hanzawa, H.; Hata, T. J. Org. Chem. 1993, 58, 7632.
8. For related programs, see: (a) Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582.
9. (b) Fürstner, A.; Kirk, D.; Fenster, M. D. B.; Aïssa, C.; De Souza, D.; Muller, O. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8103.
10. Butenandt, A.; Hallmann, G.; Beckmann, R. Chem. Ber. 1957, 90, 1120.
11. van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; van Leusen, D. Tetrahedron Lett. 1972, 13, 5337.
12. For the preparation of 10 from p-hydroxyphenylpyruvic acid, see the Supporting Information.
13. Fürstner, A.; Hupperts, A.; Ptock, A.; Janssen, E. J. Org. Chem. 1994, 59, 5215.
14. (a) Fürstner, A.; Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2442.
15. (b) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
16. (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
17. (b) Fürstner, A.; Jumbam, D. N. Tetrahedron 1992, 48, 5991.
18. (c) Fürstner, A.; Ernst, A. Tetrahedron 1995, 51, 773.
19. (d) Fürstner, A.; Ernst, A.; Krause, H.; Plock, A. Tetrahedron 1996, 52, 7329.
20. (e) Fürstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637.
21. (f) Fürstner, A.; Jumbam, D. N. J. Chem. Soc., Chem. Commun. 1993, 211.
22. Fürstner, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 164.
23. For pertinent reviews on carbazoles, see: (a) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
24. (b) Kawasaki, T.; Sakamoto, M. J. Ind. Chem. Soc. 1994, 71, 443.
25. Rawal, V. H.; Jones, R. J.; Cava, M. P. Tetrahedron Lett. 1985, 26, 2423.
26. Precedence: Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817.
27. 4COCl or the corresponding Weinreb amide were unsuccessful.
28. Compare: Bringmann, G.; Tasler, S.; Endress, H.; Kraus, J.; Messer, K.; Wohlfarth, M.; Lobin, W. J. Am. Chem. Soc. 2001, 123, 2703.
29. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
30. Liu, Y.; Lien, I. F.; Ruttgaizer, S.; Dove, P.; Taylor, S. D. Org. Lett. 2004, 6, 209.
31. Brooks, P. R.; Wirtz, M. C.; Vetelino, M. G.; Rescek, D. M.; Woodworth, G. F.; Morgan, B. P.; Coe, J. W. J. Org. Chem. 1999, 64, 9719.