Diastereomeric Resolution of a Racemic Biaryl Boronic Acid and Its Application to Divergent Asymmetric Total Syntheses of Some Axially Chiral Natural Products

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author Cheol-Hong Cheon
journal Advanced Synthesis & Catalysis 2016, 358(4), 549–554
Homepage https://sites.google.com/site/cheonresearchlab/


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The asymmetric total syntheses of deshydroxy-tetramethylcupressuflavone and desmethylkotanin and the synthesis of a key intermediate in the previous synthesis of hibarimicinone were described using an axially chiral biaryl boronic acid, prepared by the diastereomeric resolution of the corresponding rac-boronic acid, as a common intermediate. Conversion of the boronic acid moiety into either a hydrogen atom or a hydroxy group by protodeboronation or oxidation enabled us to complete the total syntheses of deshydroxytetramethylcupressuflavone and desmethylkotanin and synthesis of a key intermediate in the previous total synthesis of hibarimicinone, respectively.




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