γ–Lactones Upon Double Nucleophilic Additions of Bis(TMS)Ketene Acetals to Π–systems and Access to New–towards Cancer Cells Cytotoxic–Endoperoxide Lactones
Henri Rudler,1* Eugenia Aldeco–Pérez,2 Andrée Parlier,1 Cecilio Álvarez,2 Patrick Chaquin,1 Patrick Herson,1 Alfredo Toscano,2 and María–Teresa Ramírez–Apan2
1 Université Pierre et Marie Curie, Laboratoire de Chimie Organique, UMR 7611–CNRS, 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 diene–lactones or cyclohexenone–lactones. 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, γ–lactones, 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 dieno–lactonas como ciclohexenona–lactonas. 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, γ–lactonas, acetales de bis(trimetilsilil)cetena, complejos de tricarbonilcromo, doble adición nucleofílica.
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