Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 48, Pages 19782-19787Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3084708
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Funding
- NIH [GM-073855]
- NIGMS CMLD Initiative [P50 GM067041]
- Intramural Research Program of NIH, National Cancer Institute, Center for Cancer Research
- Developmental Therapeutics Program, Division of Cancer Diagnosis and Treatment
- Vertex Pharmaceuticals, Inc.
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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.
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