AI Article Synopsis
- A novel method was developed to synthesize gliocladin C and related alkaloids, utilizing a unique nucleophilic addition followed by Friedel-Crafts alkylation to create a key quaternary center.
- This process involved chemoselective reduction and cyclization to achieve a crucial hexahydropyrrolo[2,3-b]indole diketopiperazine intermediate.
- The strategy resulted in the most efficient synthesis of (±)-gliocladin C, (±)-T988C, and (±)-gliocladine C reported to date.
Article Abstract
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.
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| http://dx.doi.org/10.1021/acs.orglett.7b00735 | DOI Listing |
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