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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
An enantioselective route to paeonilactone A via palladium- and copper-catalyzed reactions
C Jonasson1, M Rönn, J E Bäckvall
1Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Abstract:
We herein report on a formal total synthesis of paeonilactone A involving palladium-, copper-, and enzyme-catalyzed reactions starting from 1,3-cyclohexadiene. The key step in the synthesis, a palladium(II)-catalyzed 1,4-oxylactonization of a conjugated diene, simultaneously introduces two of the oxygen substituents required for the target molecule. The synthesis also includes our recently developed copper(I)-catalyzed cross-coupling reaction between dienyltriflates with Grignard reagents, introducing one of the methyl groups present in the target molecule. This new approach toward paeonilactone A allows complete control of all four stereogenic centers and is the first enantioselective route toward paeonilactone A starting from an achiral substrate.
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