5 years ago

Syntheses of Gliocladin C and Related Alkaloids

Syntheses of Gliocladin C and Related Alkaloids
Timothy R. Hodges, Stephen F. Martin, Noah M. Benjamin
A unique approach to gliocladin C and related alkaloids was developed that features 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 set the key quaternary center. Chemoselective oxindole reduction and cyclization delivered a pivotal hexahydropyrrolo[2,3-b]indole diketopiperazine intermediate that was readily converted into (±)-gliocladin C, (±)-T988C, and (±)-gliocladine C, culminating in the shortest approach to these alkaloids reported to date.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00735

DOI: 10.1021/acs.orglett.7b00735

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