Total synthesis of kealiiquinone: the regio-controlled strategy for accessing its 1-methyl-4-arylbenzimidazolone core

A practical, concise and straightforward total synthesis of kealiiquinone 1, a naphtho[2,3- ]imidazole alkaloid obtained from the Micronesian marine sponge sp. was accomplished. The squaric acid chemistry to construct the 1,4-quinoid ring and the regioselective -methylation through a benzo[ ][1,2,5]...

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Bibliographic Details
Published in:RSC advances 2018-01, Vol.8 (54), p.30761-30776
Main Authors: Ramadoss, Velayudham, Alonso-Castro, Angel J, Campos-Xolalpa, Nimsi, Ortiz-Alvarado, Rafael, Yahuaca-Juárez, Berenice, Solorio-Alvarado, César R
Format: Article
Language:English
Subjects:
Chemistry
Imidazole
Methylation
Organic chemistry
Synthesis
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Summary:A practical, concise and straightforward total synthesis of kealiiquinone 1, a naphtho[2,3- ]imidazole alkaloid obtained from the Micronesian marine sponge sp. was accomplished. The squaric acid chemistry to construct the 1,4-quinoid ring and the regioselective -methylation through a benzo[ ][1,2,5]selenadiazolium heterocycle are the key features in this report. The full details of the representative approaches involving the different attempted synthetic strategies are also presented. Finally a successful total synthesis of this complex secondary metabolite is described.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra06676k