Chaetoglobin A is natural product isolated from endophytic fungus chaetomium globosum which lives in the stem of Imperata cylindrical. It features two quaternary stereocenters in the highly oxygenated 2H-isoquinoline-6,8-dione moieties and a chiral axis that connects these two identical halves. This class of dimeric azaphilone alkaloids has not been synthesized to date. Our approach centers on an asymmetric oxidative phenol coupling reaction to establish the chiral biaryl portion, followed by Lewis acid catalyzed oxidative dearomatization to generate bicyclic heterocycles and quaternary stereocenters. It allows us to synthesize the desired natural product successfully within 12 steps overall.

Total synthesis of chaetoglobin A via asymmetric oxidative phenol coupling reaction

253rd National Meeting (2017)

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