Concise synthesis of deformylflustrabromine, a marine indole alkaloid, through a 2-propynyl dicobalt hexacarbonyl complex

Chemistry Letters

Volumn 40, Issue 10, 2011, Pages 1079-1081

  Isaji, Hisaaki ^a   Nakazaki, Atsuo ^a   Isobe, Minoru ^a   Nishikawa, Toshio ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80053261674     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.1079     Document Type: Article

References (33)

1. A. Rahman, A. Basha, Indole Alkaloids, Harwood Academic Publishers, Amsterdam, 1998.
2. Recent review of terpene indole alkaloids: M. Ishikura, K. Yamada, Nat. Prod. Rep. 2009, 26, 803, and referenced cited therein.
3. For a review of prenylated indole, see: S.-M. Li, Nat. Prod. Rep. 2010, 27, 57.
4. a) J. M. Schkeryantz, J. C. G. Woo, P. Siliphaivanh, K. M. Depew, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11964.
5. J. M. Schkeryantz, J. C. G. Woo, S. J. Danishefsky, J. Am. Chem. Soc. 1995, 117, 7025.
6. a) K. Tomita, A. Terada, R. Tachikawa, Heterocycles 1976, 4, 733.
7. F. Yamada, Y. Fukui, D. Shinmyo, M. Somei, Heterocycles 1993, 35, 99.
8. For synthesis of 2-reverse prenylindole not from indole, see: a) H. Plieninger, H. Sirowej, Chem. Ber. 1971, 104, 2027.
9. N. Takamatsu, S. Inoue, Y. Kishi, Tetrahedron Lett. 1971, 12, 4665.
10. K. A. Miller, T. R. Welch, T. J. Greshock, Y. Ding, D. H. Sherman, R. M. Williams, J. Org. Chem. 2008, 73, 3116.
11. a) T. Lindel, L. Bräuchle, G. Golz, P. Böhrer, Org. Lett. 2007, 9, 283.
12. J.-S. Kim, A. Padnya, M. Weltzin, B. W. Edmonds, M. K. Schulte, R. A. Glennon, Bioorg. Med. Chem. Lett. 2007, 17, 4855.
13. M. R. Luzung, C. A. Lewis, P. S. Baran, Angew. Chem., Int. Ed. 2009, 48, 7025.
14. For other example of reverse prenylation at the N-1 position of indoles, see: H. Sugiyama, F. Yokokawa, T. Aoyama, T. Shioiri, Tetrahedron Lett. 2001, 42, 7277.
15. K. Sugino, A. Nakazaki, M. Isobe, T. Nishikawa, Synlett 2011, 647.
16. a) L. Peters, G. M. König, H. Terlau, A. D. Wright, J. Nat. Prod. 2002, 65, 1633.
17. N. Lysek, E. Rachor, T. Lindel, Z. Naturforsch., C: J. Biosci. 2002, 57 c, 1056.
18. L. Peters, A. D. Wright, A. Krick, G. M. König, J. Chem. Ecol. 2004, 30, 1165.
19. T. Hosoe, T. Itabashi, N. Kobayashi, S.-i. Udagawa, K.-i. Kawai, Chem. Pharm. Bull. 2006, 54, 185.
20. J. A. Laakso, J. B. Gloer, D. T. Wicklow, P. F. Dowd, J. Org. Chem. 1992, 57, 2066.
21. R. T. Gallagher, J. Clardy, B. J. Wilson, Tetrahedron Lett. 1980, 21, 239.
22. R. F. Lockwood, K. M. Nicholas, Tetrahedron Lett. 1977, 18, 4163.
23. For reviews of Nicholas reaction, see: a) K. M. Nicholas, Acc. Chem. Res. 1987, 20, 207.
24. B. J. Teobald, Tetrahedron 2002, 58, 4133.
25. Nicholas reaction of indole with a cobalt propargylium tetrafluoroborate: K.-D. Roth, Synlett 1993, 529.
26. M. Nakagawa, J. Ma, T. Hino, Heterocycles 1990, 30, 451.
27. Supporting Information is available electronically on the CSJ-Journal Website, http://www.csj.jp/journals/chem-lett/index.html.
28. The possibility of converting an N-1-prenylated indole intermediate to a C-2-prenylated indole derivative in a biosynthesis is discussed, see: H. Zou, X. Zheng, S.-M. Li, J. Nat. Prod. 2009, 72, 44.
29. S. Hosokawa, M. Isobe, Tetrahedron Lett. 1998, 39, 2609.
30. a) O. R. Suárez-Castillo, M. Sánchez-Zavala, M. Meléndez-Rodríguez, E. Aquino-Torres, M. S. Morales-Ríos, P. Joseph-Nathan, Heterocycles 2007, 71, 1539.
31. S. Kajii, T. Nishikawa, M. Isobe, Chem. Commun. 2008, 3121.
32. a) L. S. Santos, R. A. Pilli, Tetrahedron Lett. 2001, 42, 6999.
33. N. M. Yoon, H. C. Brown, J. Am. Chem. Soc. 1968, 90, 2927.