A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11), in ten steps and 11% overall yield from isatin, is reported. In addition, the ETP natural product (+)-gliocladine C (6) is prepared in six steps and 29% yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of (+)-gliocladine C (6) constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.
The first total synthesis of a member of the plectosphaeroic acid family of fungal natural products is reported. Key steps include the late-stage formation of the hindered N6–C9″ bond and stereoselective introduction of the two methylthio substituents.
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