Total synthesis of kealiiquinone: the regio-controlled strategy for accessing its 1-methyl-4-arylbenzimidazolone core
Open Access
- 31 August 2018
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in RSC Advances
- Vol. 8 (54), 30761-30776
- https://doi.org/10.1039/c8ra06676k
Abstract
A practical, concise and straightforward total synthesis of kealiiquinone 1, a naphtho[2,3-d]imidazole alkaloid obtained from the Micronesian marine sponge Leucetta sp. was accomplished. The squaric acid chemistry to construct the 1,4-quinoid ring and the regioselective N-methylation through a benzo[c][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.Funding Information
- Consejo Nacional de Ciencia y Tecnología (CB-2013/220836)
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