Synthesis of Chamaecypanone C Analogues from <i>in Situ</i>-Generated Cyclopentadienones and Their Biological Evaluation

Abstract

A rhodium-catalyzed dehydrogenation protocol for the conversion of 3,5-diarylcyclopentenones to the corresponding 2,4-diarylcyclopentadienones has been developed. With this protocol, analogues of the cytotoxic agent chamaecypanone C have been synthesized <i>via</i> Diels–Alder cycloaddition between the cyclopentadienones and <i>in situ</i>-generated <i>o</i>-quinols. Biological evaluation of these analogues revealed a compound with higher activity as a microtubule inhibitor and cytotoxic agent in comparison with the parent structure