SciELO - Scientific Electronic Library Online

 
vol.55 número1Cyanide Degradation by Direct and Indirect Electrochemical Oxidation in Electro-active Support Electrolyte Aqueous SolutionsConstituents of Organic Extracts of Cuphea hyssopifolia índice de autoresíndice de assuntospesquisa de artigos
Home Pagelista alfabética de periódicos  

Serviços Personalizados

Journal

Artigo

Indicadores

Links relacionados

  • Não possue artigos similaresSimilares em SciELO

Compartilhar


Journal of the Mexican Chemical Society

versão impressa ISSN 1870-249X

J. Mex. Chem. Soc vol.55 no.1 Ciudad de México Jan./Mar. 2011

 

Article

 

Syntheses of Three Mono–Brominated Enamide Analogs of Natural Alkaloids Isolated from the Tasmanian Marine Bryozoan Amathia Wilson

 

Moisés Ramírez–Osuna, Oscar F. Narvaez–Garayzar, Ratnasamy Somanathan and Gerardo Aguirre*

 

Centro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, Tijuana, B. C. 22500, México. Tel: (664) 6233772, Fax: (664) 6234043.

 

Received June 14, 2010.
Accepted December 17, 2010.

 

Abstract

Synthesis of three brominated enamides, analogs of natural alkaloids isolated from the Tasmanian marine bryozoan Amathia Wilson, were prepared by a sequence of reactions starting from 3–hydroxybenzaldehyde.

Keywords: brominated enamides, amathamides.

 

Resumen

Síntesis de tres enamidas bromadas, análogas a los alcaloides naturales aislados del briozoo Amathia Wilson de los mares de Tasmania. Esta síntesis se llevo a cabo a través de una secuencia de reacciones que parten del 3–hidroxibenzaldehído.

Palabras clave: enamidas bromadas, amathamidas.

 

DESCARGAR ARTÍCULO EN FORMATO PDF

 

Acknowledgement

We gratefully acknowledge support for this project from Dirección General de Educación Superior Tecnológica (DGEST) 2536.09–P.

 

References

1. Chatterjee, A.; Chakrabarty, M.; Kundu, A. B. Adrian Aust. J. Chem., 1975, 28, 457–460.         [ Links ]

2. Govindanchari, T.; Premila, M. Phytochemistry 1983, 22, 755–757.         [ Links ]

3. (a) Burke, B. A.; Philip, S. Heterocycles 1985, 23, 257–260.         [ Links ] (b) Burke, B. A.; Parking, H. Tetrahedron Lett. 1978, 2723–2726.         [ Links ]

4. Ohjuma, K.; Anzai, K.; Anzai, K.; Suzuki, S. J. Antibiot. 1962, 15, 115.         [ Links ]

5. Umezawa, H.; Imoto, M.; Sawa, T.; Isshiki, K.; Matsuda, N.; Uchidda, T.; Linuma, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1986, 39, 170–173.         [ Links ]

6. Kagamizone, T. Sakai, N.; Arai, K.; Kobinata, K.; Osada, H. Tetrahedron Lett. 1997, 38, 1223–1226.         [ Links ]

7. Kirkuk, P.; Moore, R. Tetrahedron Lett. 1983, 24, 2087–2090.         [ Links ]

8. (a) Andersen, R. J. Tetrahedron Lett. 1978, 19, 2545–2544;         [ Links ] (b) Andersen, R. J.; Stonard, R. J. Can. J. Chem. 1979, 57, 2325–2328.         [ Links ]

9. Bruening, R. C.; Oltz, E. M.; Furukawa, J.; Nakanishi, K.; Kustin, K. J. Nat. Prod. 1986, 49, 193–204.         [ Links ]

10. Oltz, E. M.; Bruening, R. C.; Smith, M. J.; Kusting, K.; Nakanishi, K. J. Am. Chem. Soc. 1988, 110, 6162–6172.         [ Links ]

11. Azumi, K.; Yokisawa, H.; Ishii, S. Biochemistry 1990, 29, 159–165.         [ Links ]

12. (a) Galanis, D. L.; McKee, T. C.; Pannell, L. K.; Cardellina, J. H.; Boyd, M. R. J. Org. Chem. 1997, 62, 8968–8969 (b) Kim.         [ Links ] J. W.; Shinya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Org. Chem. 1999, 64, 153–155.         [ Links ]

13. Blackman, A. J.; Matthews, D. J. Heterocycles 1985, 23, 2829–2832.         [ Links ]

14. Blackman, A. J.; Green, R. D. Aust. J. Chem. 1987, 40, 1655–1662.         [ Links ]

15. Blackman, A. J.; Eldershaw, T. P. D.; Garland, S. M. Aust. J. Chem. 1993, 46, 401–405.         [ Links ]

16. Narkowicz, C.; Blackman, A. J.; Lacey, E.; Gill, J.; Heiland, K. Proceedings of ICNP–2002–Trabzon / Türkiye 2002, 26–29.         [ Links ]

17. Ramírez–Osuna M.; Chávez, D.; Hernández, L.; Molins, E.; Somanathan R. Aguirre. G. Molecules 2005, 10, 295–301.         [ Links ]

18. Ramirez–Osuna, M.; Aguirre, G.; Somanathan, R.; Molins, E. Tetrahedron: Asymmetry 2002, 13, 2261–2266.         [ Links ]

19. G. Aguirre, R. Somanathan and L. H. Hellberg. J. Fluorine Chem. 1998, 90, 5–8.         [ Links ]

20. Data collected at 294 K using highly oriented graphite crystal monochromated MoK α radiation, The structure was solved by direct methods and non–hydrogen atoms were refined anisotropically. In the final least–squares refinement cycle on F, R = 7.79%, wR2 = 20.77%. The crystal data are a = 7.790(3) Å b = 9.113(2) Å, c = 9.968(4) Å, α = 900, β = 97.06 (3)0, γ = 900, V = 702.2(4) Å3, space group P21/n. CCDC number 779842 for compound 8c.

Creative Commons License Todo o conteúdo deste periódico, exceto onde está identificado, está licenciado sob uma Licença Creative Commons