Stereoselective furan-iminium cation cyclization in the construction of the core structure of manzamine A

Organic Letters

Volumn 8, Issue 1, 2006, Pages 27-30

  Tokumaru, Kazuyuki ^a   Arai, Shigeru ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; CATION; FURAN DERIVATIVE; IMINE; INDOLE DERIVATIVE; MANZAMINE A; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; X RAY DIFFRACTION;

CARBAZOLES; CATIONS; CYCLIZATION; FURANS; IMINES; INDOLES; MODELS, MOLECULAR; PYRROLES; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 30944458459     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052387m     Document Type: Article

References (29)

1. For review, see; Hu, J.-F.; Hamann, M. T.; Hill, R.; Kelly, M. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: New York, 2003; Vol. 60, p 207.
2. Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G. J. Am. Chem. Soc. 1986, 108, 6404.
3. For selected studies, see: (a) Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieräugel, H. Eur. J. Org. Chem. 1999, 959.
4. (b) Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 39, 837.
5. (c) Brands, K. M. J.; DiMichele, L. M. Tetrahedron Lett. 1998, 39, 1677.
6. (d) Nakagawa, M., Torisawa, Y., Uchida, H., Nishida, A. J. Synth. Org. Chem. Jpn. 1999, 57, 1004.
7. (e) Li, S.; Yamamura, S. Tetrahedron 1998, 54, 8691.
8. (f) Bland, D.; Chambournier, G.; Dragan, V.; Hart, D. J. Tetrahedron 1999, 55, 8953.
9. (g) Clark, J. S.; Townsend, R. J.; Blake, A. J.; Teat, S. J.; Johns, A. Tetrahedron Lett. 2001, 42, 3235.
10. (h) Herdemann, M.; Al-Mourabit, A.; Martin, M.-T.; Marazano, C. J. Org. Chem. 2002, 67, 1890.
11. (i) Magnus, P.; Fielding, M. R.; Wells, C.; Lynch, V. Tetrahedron Lett. 2002, 43, 947.
12. (j) Coldham, I.; Pih, S. M.; Rabot, R. Synlett 2005, 1743.
13. (a) Winkler, J. D.; Axten, J. M. J. Am. Chem. Soc. 1998, 120, 6425.
14. (b) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866.
15. (c) Humphrey, J. M.; Liao, Y.; Ali, A.; Rein, T.; Wong, Y.-L.; Chen, H.-J.; Courtney, A. K.; Martin, S. F. J. Am. Chem. Soc. 2002, 124, 8584.
16. (a) Nagata, T.; Nakagawa, M.; Nishida, A. J. Am. Chem. Soc. 2003, 125, 7484.
17. (b) Ono, K.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2004, 43, 2020.
18. For selected examples of furan-iminium cation cyclization, see: (a) Cassidy, M. P.; Özdemir, A. D.; Padwa, A. Org. Lett. 2005, 7, 1339.
19. (b) Tanis, S. P.; Deaton, M. V.; Dixon, L. A.; McMills, M. C.; Raggon, J. W.; Collins, M. A. J. Org. Chem. 1998, 63, 6914.
20. (c) Martin, S. F. Acc. Chem. Res. 2002, 35, 895.
21. Nagata, T.; Nishida, A.; Nakagawa, M. Tetrahedron Lett. 2001, 42, 8345.
22. Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 50, p 1.
23. Pedregal, C.; Ezquerra, J.; Escribano, A.; Carreño, M. C., Ruano, J. L. G. Tetrahedron Lett. 1994, 35, 2053.
24. The diastereoselectivity of hydrogenation was catalyst- and solvent-dependent. For example, hydrogenation using Pd/C as a catalyst in AcOEt gave the product in 84% yield and α-H:β-H ratio was 1:1.5.
25. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
26. The structure of 15 and 17 were determined by X-ray analysis after conversion to 16 and 20 (Figure 1 and Scheme 4). The structure of 18 was determined by NMR analysis (see Supporting Information).
27. Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 109, 7881.
28. Both Winkler and we successfully introduced C1 unit at C10 by α-acylation. See refs 3e and 4a. These unsuccesssful results might be attributed to the bulkiness of the tetrasubstituted center at C12.
29. Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209.