Synthesis of chamaecypanone C analogues from in situ-generated cyclopentadienones and their biological evaluation

Suwei Dong, Tian Qin, Ernest Hamel, John A. Beutler, John A. Porco

Research output: Contribution to journalArticle

19 Scopus citations

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 via Diels-Alder cycloaddition between the cyclopentadienones and in situ-generated o-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.

Original languageEnglish (US)
Pages (from-to)19782-19787
Number of pages6
JournalJournal of the American Chemical Society
Volume134
Issue number48
DOIs
StatePublished - Dec 5 2012

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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