Enantioselective Synthesis of (+)-Chamaecypanone C: A Novel Microtubule Inhibitor


  • Financial support from the National Institutes of Health (GM-073855 and P50 GM067041), Wyeth Pharmaceuticals, Merck Research Laboratories, and the NCI intramural research program is gratefully acknowledged. We thank the Developmental Therapeutics Program at the NCI for the 60-cell assay, ThalesNano, Inc. (Budapest, Hungary) for assistance with the continuous-flow hydrogenation reactor, and Prof. Dr. Corey Stephenson (Boston University) for helpful discussions.


A bicycle built for tubulin: The total synthesis of (+)-chamaecypanone C has been achieved by using a tandem retro-Diels–Alder/Diels–Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)-chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.

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