5625-41-2Relevant articles and documents
Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids
Hodges, Timothy R.,Benjamin, Noah M.,Martin, Stephen F.
, p. 3329 - 3338 (2018/04/19)
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.