Abstract
Meet the popular anticancer drug Taxol’s quirky cousin: canataxpropellane. Chemists at the University of Konstanz have now synthesized the elusive compound for the first time, creating enough of the taxane for scientists to study its bioactivity (Science 2020, DOI: 10.1126/science.aay9173). Because canataxpropellane’s natural source, the Taxus canadensis shrub, ekes out the compound in minuscule quantities, scientists haven’t been able to evaluate its biological properties. Even though it has just 24 carbon atoms, canataxpropellane’s complex architecture makes it a beast to synthesize. It has Taxol’s core skeleton, but it also contains three additional C–C bonds that bridge the compound. Those three bonds “totally change the overall strategy of approaching the molecule” so that it must be distinct from Taxol syntheses, says Tanja Gaich, who led the synthetic effort. Canataxpropellane’s other structural challenges include two propellanes—motifs in which three rings share a single C–C bond. Canataxpropellane has 12 contiguous stereocenters. Five of
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