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Journal of the Mexican Chemical Society

Print version ISSN 1870-249X

J. Mex. Chem. Soc vol.49 n.2 México  2005

 

Short Report

 

Short Synthesis of a New Cyclopentene-1,3-dione Derivative Isolated from Piper carniconnectivum

 

Luiz C. Dias*, Simone B. Shimokomaki and Robson T. Shiota

 

Instituto de Química, Universidade Estadual de Campinas, CP 6154, 13083-970 Campinas - SP, Brazil. * e-mail: ldias@iqm.unicamp.br

 

Received: September 20, 2004
Published on the web: March 30, 2005

 

Abstract

The total synthesis of cyclopentene-1,3-dione (1), a new natural cyclopentenedione derivative isolated from the roots of Piper carniconnectivum, is described in 8 steps and 11% overall yield from 2-acetylfuran, giving a 57:43 mixture of the two possible geometric isomers 1a and 1b.

Keywords: aldol reaction, allylic alcohol oxidation, cyclopentenedione derivative, Piper carniconnectivum

 

Resumo

А síntese total da ciclopentenodiona (1), isolada das raízes de Piper carniconnectivum, é descrita em 8 etapas e 11% de rendimento global a partir do 2-acetilfurano, fornecendo uma mistura 57:43 dos dois possíveis isômeros geométricos 1a e 1b.

 

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References

1. Facundo, V. A.; Sá , A. L.; Silva, S. A. F.; Morais, S. M.; Matos, C. R. R.; Braz-Filho, R.; J. Braz.. Chem. Soc. 2004, 15, 140.         [ Links ]

2. Ribeiro, J. E. L. da S.; Hopkins, M. J. G.; Vincentin, A.; Sothers, C. A.; Costa, M. A. da S.; de Brito, J. M.; de Souza, M. A. D.; Martins, L. H. P.; Lohmann, L. G.; Assunção, P. A. C. L.; Pereira, E. da C.; Mesquita, M. R.; Procópio, L. C.; Flora da Reserva Ducke - Guia de Identificação das Plantas Vasculares de uma Floresta de Terra-Firme na Amazônia Central, INPA-DFID: Manaus, Amazonas, Brasil, 1999. p. 181.         [ Links ]

3. For other compounds isolated from the Piper genus, see: Parmar, V. S.; Jain, S. C.; Bisht, K. S.; Jain, R.; Taneja, P.; Jha, A.; Tyagi, O. D.; Prasad, A. K.; Wengel, J.; Olsen, C. E.; Boll, P. M.; Phytochemistry 1997, 46, 597.         [ Links ]

4. The numbering of (1) as well as of each intermediate follows that suggested in reference 1.

5. West, F. G.; Gunawardena, G. U.; J. Org. Chem. 1993, 58, 2402.         [ Links ] Furylcarbinol (5) could also be obtained by the reaction of 2-lithium furan with acetaldehyde in 84% yield.

6. Piancatelli, G.; Scettri, A.; David, G.; D'Auria, M.; Tetrahedron 1978, 34, 2775;         [ Links ] West, F. G.; Gunawardena, G. U.; J. Org. Chem. 1993, 58, 5043;         [ Links ] Piancatelli, G.; D'Auria, M.; D'Onofrio, F.; Synthesis 1994, 867.         [ Links ]

7. Scettri, A.; Piancatelli, G.; D'Auria, M.; David, G.; Tetrahedron 1979, 35, 135;         [ Links ] Shono, T.; Hamaguchi, H.; Aoki, K.; Chem. Lett. 1977, 1053;         [ Links ] Csáky, A. G.; Mba, M.; Plumet, J.; J. Org. Chem. 2001, 66, 9026;         [ Links ] Csáky, A. G.; Mba, M.; Plumet, J.; Synlett 2003, 2092.         [ Links ]

8. Corey, E. J.; Gilman, N. W.; Ganem, B. E.; J. Am. Chem. Soc. 1968, 90, 5616.         [ Links ]

9. For large scale preparations of cyclopentenedione 12, the use of Jones oxidation conditions is recommended. See: Lola, D.; Belakovs, S.; Gavars, M.; Turovskis, I.; Kemme, A.; Tetrahedron 1998, 54, 1589.         [ Links ]

10. Olivieri, A. C.; González-Sierra, M.; Rúveda, E.; A.; J. Org. Chem. 1986, 51, 2824.         [ Links ]

11. Mancuso, A. J.; Swern, D.; Synthesis 1981, 165.         [ Links ]

12. New compounds and the additional isolated intermediates gave satisfactory 1H and 13C NMR, IR, HRMS and analytical data. Yields refer to chromatographically and spectroscopically homogeneous materials.

 

Notes

Dedicated to Prof. Raimundo Braz-Filho for his outstanding contributions to the field of Organic Chemistry in Brazil.

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