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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
J. Mex. Chem. Soc vol.52 no.2 Ciudad de México abr./jun. 2008
Article
γLactones Upon Double Nucleophilic Additions of Bis(TMS)Ketene Acetals to Πsystems and Access to Newtowards Cancer Cells CytotoxicEndoperoxide Lactones
Henri Rudler,1* Eugenia AldecoPérez,2 Andrée Parlier,1 Cecilio Álvarez,2 Patrick Chaquin,1 Patrick Herson,1 Alfredo Toscano,2 and MaríaTeresa RamírezApan2
1 Université Pierre et Marie Curie, Laboratoire de Chimie Organique, UMR 7611CNRS, Institut de Chimie Moléculaire FR 2769, 4 place Jussieu, CC 47, 75252 Paris Cedex 5, France.
2 Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, México D.F., México. *Responsible author: rudler@ccr.jussieu.fr.
Recibido el 16 de noviembre de 2007
Aceptado el 20 de mayo de 2008
Abstract
Arenechromium and cycloheptatrienechromium complexes react with (TMS)ketene acetals to give upon a double nucleophilic addition either dienelactones or cyclohexenonelactones. In the first case, the scope of the reaction and the stability of the dienes were examined: they could be easily transformed either in arylpropionic acids or in conjugated ketones and more interestingly, they reacted with oxygen to give new highly active cytotoxic endoperoxide lactones. Unfortunately, in the second case, no further functionalization could be achieved up to now.
Key words: Endoperoxide lactones, cytotoxic activities, γlactones, feis(TMS)ketene acetals, tricarbonylchromium complexes, double nucleophilic additions.
Resumen
Se describe la reacción entre complejos arentricarbonilcromo y cicloheptatrientricarbonilcromo con acetales de bis(trimetil silil)cetena, la cual mediante una doble adición nucleofílica conduce a la formación tanto de dienolactonas como ciclohexenonalactonas. En el primer caso, se examinó la estabilidad de los dienos: pudiendo éstos transformarse fácilmente en ácidos arilpropiónicos o en cetonas conjugadas y al reaccionar con oxígeno en nuevas endoperoxolactonas con actividad citotóxica importante. Desafortunadamente, en el segundo caso, no pudo realizarse la funcionalización posterior de dichas moléculas.
Palabras clave: Endoperoxolactonas, actividad citotóxica, γlactonas, acetales de bis(trimetilsilil)cetena, complejos de tricarbonilcromo, doble adición nucleofílica.
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