Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids

Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Tetrahedron Elsevier

Concise approach to the syntheses of (±)-gliocladin C and related diketopiperazine alkaloids

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier Ltd
ISSN
0040-4020
D.O.I.
10.1016/j.tet.2018.04.001
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

TetrahedronElsevier

Published: Jun 28, 2018

References

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