Reduction of 2,5-bis(3′-indolyl)pyrazines to 2,5-bis(3′- indolyl)piperazines: Synthesis of bisindolylpiperazine marine alkaloids dragmacidin A, B, and C

Synthesis

Volumn , Issue 1, 2006, Pages 49-54

  Tonsiengsom, Fay ^a   Miyake, Fumiko Y ^a   Yakushijin, Kenichi ^a   Horne, David A ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

Indoles; Piperazines; Pyrazines; Reductions; Total synthesis

Indexed keywords

REDUCTION; SYNTHESIS (CHEMICAL);

INDOLES; PIPERAZINES; PYRAZINES; TOTAL SYNTHESIS;

NITROGEN COMPOUNDS;

2,5 BIS(3' INDOLYL)PIPERAZINE DERIVATIVE; 2,5 BIS(3' INDOLYL)PYRAZINE DERIVATIVE; DRAGMACIDIN A; DRAGMACIDIN B; DRAGMACIDIN C; INDOLE ALKALOID; PIPERAZINE DERIVATIVE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REDUCTION;

EID: 30944462568     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918431     Document Type: Article

References (20)

1. (a) Yang, C.-G.; Huang, J.; Jiang, B. Curr. Org. Chem. 2004, 8, 1691.
2. (b) Aygün, A.; Pindur, U. Curr. Med. Chem. 2003, 10, 1113.
3. (c) Pindur, U.; Lemster, T. Curr. Med. Chem. 2001, 8, 1681.
4. Morris, S. A.; Andersen, R. J. Tetrahedron 1990, 46, 715.
5. Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. J. Nat. Prod. 1991, 54, 564.
6. Whitlock, C. R.; Cava, M. P. Tetrahedron Lett. 1994, 35, 371.
7. (a) Jiang, B.; Smallheer, J. M.; Amaral-Ly, C.; Wuonola, M. A. J. Org. Chem. 1994, 59, 6823.
8. (b) Yang, C.-G.; Wang, J.; Tang, X.-X.; Jiang, B. Tetrahedron: Asymmetry 2002, 13, 383.
9. (a) Kawasaki, T.; Enoki, H.; Matsumura, K.; Ohyama, M.; Inagawa, M.; Sakamoto, M. Org. Lett. 2000, 2, 3027.
10. (b) Kawasaki, T.; Ohno, K.; Enoki, H.; Umemoto, Y.; Sakamoto, M. Tetrahedron Lett. 2002, 43, 4245.
11. (a) Garg, N. K.; Stoltz, B. M. Tetrahedron Lett. 2005, 46, 2423.
12. For the construction of bis(indoyl)-1,2,4-triazones, see: (b) Garg, N. K.; Stoltz, B. M. Tetrahedron Lett. 2005, 46, 1997.
13. For a recent and elegant synthesis of the more structurally complex bis(indolyl)piperazine marine alkaloid, dragmacidin F, see: (c) Garg, N. K.; Caspi, D. D.; Stoltz, B. M. J. Am. Chem. Soc. 2005, 127, 5970.
14. Lyle, R. E.; Thomas, J. T. J. Org. Chem. 1965, 30, 1907.
15. (a) Gribble, G. W.; Lord, P. D.; Skotnicki, J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. J. Am. Chem. Soc. 1974, 96, 7812.
16. (b) Gribble, G. W.; Hoffman, J. H. Synthesis 1977, 859.
17. Miyake, F. Y.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3185.
18. Hogan, I. T.; Sainsbury, M. Tetrahedron 1984, 40, 681.
19. Oikawa, Y.; Yoshioka, T.; Mohri, K.; Yonemitsu, O. Heterocycles 1979, 12, 1457.
20. Miyake, F.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 2121.