Synthesis of (±)-eusynstyelamide A

Organic Letters

Volumn 12, Issue 11, 2010, Pages 2664-2667

  Barykina, Olga V ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; EUSYNSTYELAMIDE A; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HYDROCARBONS, BROMINATED; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77952981987     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100896n     Document Type: Article

References (26)

1. Tapiolas, D. M.; Bowden, B. F.; Abou-Mansour, E.; Willis, R. H.; Doyle, J. R.; Muirhead, A. N.; Liptrot, C.; Llewellyn, L. E.; Wolff, C. W. W.; Wright, A. D.; Motti, C. A. J. Nat. Prod. 2009, 72, 1115-1120
2. Swersey, J. C.; Ireland, C. M.; Cornell, L. M.; Peterson, R. W. J. Nat. Prod. 1994, 57, 842-845
3. Snider, B. B.; Song, F.; Foxman, B. M. J. Org. Chem. 2000, 65, 793-800
4. Schumacher, R. W.; Davidson, B. S. Tetrahedron 1999, 55, 935-942
5. Konda-Yamada, Y.; Okada, C.; Yoshida, K.; Umeda, Y.; Arima, S.; Sato, N.; Kai, T.; Takayanagi, H.; Harigaya, Y. Tetrahedron 2002, 58, 7851-7861
6. Stevenson, C. P.; Nielsen, L. P. C.; Jacobsen, E. N. Org. Synth. 2006, 83, 162-169
7. Sunazuka, T.; Shirahata, T.; Tsuchiya, S.; Hirose, T.; Mori, R.; Harigaya, Y.; Kuwajima, I.; Omura, S. Org. Lett. 2005, 7, 941-943
8. Tsuchiya, S.; Sunazuka, T.; Shirahata, T.; Hirose, T.; Kaji, E.; Omura, S. Heterocycles 2007, 72, 91-94
9. Indole (with a nucleophilicity N = 5.55) reacted with styrene oxide in trifluoroethanol at 80 °C for 4 h to give the alkylation product β-phenyl-1 H -indole-3-ethanol in 67% yield. Under the same conditions, 5-bromoindole (N = 4.38) gave the alkylation product in only 45% yield after 72 h. The reaction of 6-bromoindole was not reported. See
10. Westermaier, M.; Mayr, H. Chem. - Eur. J. 2008, 14, 1638-1647
11. Sarabia, F.; Sainchez-Ruiz, A.; Chammaa, S. Bioorg. Med. Chem. 2005, 13, 1691-1705
12. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019-8022
13. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272-7276
14. De Munari, S.; Frigerio, M.; Santagostino, M. J. Org. Chem. 1996, 61, 9272-9279
15. Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538
16. BranIa, M. F.; Garcia, M. L.; López, B.; de Pascual-Teresa, B.; Ramos, A.; Pozuelo, J. M.; Dominguez, M. T. Org. Biomol. Chem. 2004, 2, 1864-1871
17. Bachmann, S.; Knudsen, K. R.; Jørgensen, K. A. Org. Biomol. Chem. 2004, 2, 2044-2049
18. Lee, H.-H.; Takai, T.; Senda, H.; Kuwae, A.; Hanai, K. J. Mol. Struct. 1998, 449, 69-75
19. Stock, A. M.; Donahue, W. E.; Amstutz, E. D. J. Org. Chem. 1958, 23, 1840-1848
20. Frebault, F.; Simpkins, N. S.; Fenwick, A. J. Am. Chem. Soc. 2009, 131, 4214-4215
21. Gonzalez, J. F.; de la Cuesta, E.; AvendanIo, C. Tetrahedron 2008, 64, 2762-2771
22. Cahnmann, H. J.; Funakoshi, K. Biochemistry 1970, 9, 90-98
23. Jefford, C. W.; Knöpfel, W.; Cadby, P. A. J. Am. Chem. Soc. 1978, 100, 6432-6436
24. Jefford, C. W.; Knöpfel, W.; Cadby, P. A. Tetrahedron Lett. 1978, 3585-3588
25. Wratten, S. J.; Wolfe, M. S.; Andersen, R. J.; Faulkner, D. J. Antimicrob. Agents Chemother. 1977, 11, 411-414
26. Rasmussen, T.; Jensen, J.; Anthoni, U.; Christophersen, C.; Nielsen, P. H. J. Nat. Prod. 1993, 56, 1553-1558