A unique approach to the diketopiperazine indole alkaloid (±)-gliocladin C was developed and applied to formal syntheses of the related alkaloids (±)-gliocladine C and (±)-T988C. The key features of the strategy include an unprecedented nucleophilic addition of a diketopiperazine to an isatin derivative followed by a Friedel-Crafts alkylation of the resultant tertiary alcohol with indole to establish the critical quaternary center. Subsequent reduction of the intermediate oxindole moiety and cyclization then delivered a pivotal hexahydropyrrolo[2,3-b]indole diketopiperazine intermediate that was readily converted into (±)-gliocladin C as well as racemic versions of key intermediates in the Overman syntheses of (+)-gliocladine C and (+)-T988C.
Tetrahedron – Elsevier
Published: Jun 28, 2018
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