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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:


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



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



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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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.

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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.



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

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