Synthesis of novel polycyclic indolyldiamines

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1911-1913

  Cutri, Sabrina ^a   Diez, Anna ^b   Bonin, Martine ^a   Micouin, Laurent ^a   Husson, Henri Philippe ^a  

^a FACULTÉ DES SCIENCES PHARMACEUTIQUES ET BIOLOGIQUES   (France)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLEAMINE; OXAZOLOPIPERIDINE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; PHASE TRANSITION; PRECURSOR; STEREOCHEMISTRY; SYNTHESIS;

EID: 19544380069     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047408b     Document Type: Article

References (32)

1. For a recent review, see: (a) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2581.
2. For selected leading references, see: (b) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640,
3. (c) Bloch, R. Chem. Rev. 1998, 98, 1407.
4. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
5. (e) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
6. (a) Michalson, E. T.; Szmuszkovicz, J. Prog. Drug Res. 1989, 33, 135.
7. (b) Wong, E.; Giandomenico, C. M. Chem. Rev. 1999, 99, 2451.
8. (a) Cutri, S.; Bonin, M.; Micouin, L.; Froelich, O.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 2000, 41, 1179.
9. (b) Cutri, S.; Bonin, M.; Micouin, L.; Chiaroni, A.; Husson, H.-P. J. Org. Chem. 2003, 68, 2645.
10. (a) Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Olson, R. M.; Knauer, C. S.; Chio, C. L.; Hyslop, D. K.; Campbell, J. E.; Fitzgerald, L. W.; Nichols, N. F.; Svensson, K. A.; McCall, R. B.; Haber, C. L.; Kagey, M. L.; Dinh, D. M. Bioorg. Med. Chem. Lett. 2003, 2369.
11. (b) Frédérich, M.; Jacquier, M.-J.; Thépenier, P.; De Mol, P.; Philippe, G.; Delaude, C.; Angenot, L.; Zèches-Hanrot, M. J. Nat. Prod. 2002, 65, 1382.
12. (c) Bennasar, M.-L.; Jimenez, J.-M.; Vidai, B.; Sufi, A.; Bosch, J. J. Org. Chem. 1999, 64, 9605.
13. Isolation eudistomins: (a) Rinehart, K. L., Jr.; Kobayashi, J.; Harbour, G. C.; Hughes, R. G., Jr.; Mizsak, S. A.; Scahill, T. A. J. Am. Chem. Soc. 1984, 106, 1524.
14. Biological activities: (b) Van Maerseveen, J. H.; Hermkens, P. H. H.; De Clercq, E.; Balzarini, J.; Scheeren, H. W.; Kruse, C. G. J. Med. Chem. 1992, 55, 3223.
15. Synthesis and analogues: (c) Van Maerseveen, J. H.; Scheeren, H. W.; De Clercq, E.; Balzarini, J.; Kruse, C. G. Bioorg. Med. Chem. 1997, 5, 955.
16. (d) Liu, J.-J.; Hino, T.; Tsuruoka, A.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 3487.
17. (e) Yamashita, T.; Tokuyama, H.; Fukuyama, T. Synlett 2003, 5, 738.
18. (f) Kurihara, T.; Sakamoto, Y.; Kimura, T.; Ohishi, H.; Harusawa, S.; Yoneda, R.; Suzutani, T.; Azuma, M. Chem. Pharm. Bull. 1996, 44, 900.
19. For a recent review on the synthesis of heterocycles based on iminium ion cyclizations, see: Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
20. Froelich, O.; Desos, P.; Bonin, M.; Quirion, J.-C.; Husson, H.-P. J. Org. Chem. 1996, 67, 6700.
21. Compound 8 could be characterized by NMR, but all attempts of chromatographic purifications led to its rearrangement or degradation.
22. 3b
23. Sundberg, R. J.; Broome, R.; PowersWalters, C.; Schnur, D. J. Heterocyl. Chem. 1981, 18, 807.
24. Katritzky, A. R.; Akutagawa, K. Tetrahedron Lett. 1985, 26, 5935.
25. For a similar desulfonylation reaction, followed by an N to C rearrangement, see: (a) Rubiralta, M.; Diez, A.; Vila, C. Tetrahedron 1990, 46, 4443.
26. (b) Rubiralta, M.; Diez, A.; Bosch, J.; Solans, X. J. Org. Chem. 1989, 54, 5591.
27. For selected examples, see: (a) Melnyck, P.; Legrand, B.; Gasche, J.; Ducrot, P.; Thai, C. Tetrahedron 1995, 51, 1941.
28. (b) Suzuki, H.; Iwata, C.; Sakurai, K.; Tokumoto, K.; Takahashi, H.; Hanada, M.; Yokoyama, Y.; Murakami, Y. Tetrahedron 1997, 53, 1593.
29. (c) Suzuki, H.; Yokoyama, Y.; Miyagi, C.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 2170.
30. For an example of the use of glyoxal as a bridging agent, see: Alexakis, A.; Tranchier, J.-P.; Lensen, N.; Mangeney, P. J. Am. Chem. Soc. 1995, 117, 10767 and references therein.
31. (a) Dinsmore, C. J.; Beshore, D. C. Org. Prep. Proced. Int. 2002, 34, 367.
32. (b) Dinsmore, C. J.; Bergman, J. M.; Bogusky, M. J.; Culberson, J. C.; Hamilton, K. A.; Graham, S. L. Org. Lett. 2001, 3, 865.