Total Synthesis of (+)-Gliocladin C Enabled by Visible-Light Photoredox Catalysis


  • Financial support for this research from the NIH-NIGMS (R01-GM096129), Boston University, and Boehringer Ingelheim is gratefully acknowledged. C.R.J.S. is a fellow of the Alfred P. Sloan Foundation. L.F. thanks the Novartis Institutes for BioMedical Research for a graduate fellowship. NMR (CHE-0619339) and MS (CHE-0443618) facilities at BU are supported by the NSF.


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Lighting the way: In a 10-step total synthesis of the title compound, visible-light photoredox catalysis enabled the construction of the key bond by facilitating the direct coupling of a pyrroloindoline-derived radical with a substituted indole (see scheme; Boc=tert-butyloxycarbonyl, Cbz=benzyloxycarbonyl, DMF=N,N′-dimethylformamide). This represents the first implementation of visible-light photoredox catalysis in a total synthesis.