Total synthesis of kealiiquinone: the regio-controlled strategy for accessing its 1-methyl-4-arylbenzimidazolone core. Issue 54 (31st August 2018)

• Record Type: Journal Article
• Authors: Ramadoss, Velayudham; Alonso-Castro, Angel J.; Campos-Xolalpa, Nimsi; Ortiz-Alvarado, Rafael; Yahuaca-Juárez, Berenice; Solorio-Alvarado, César R.
• Is Part Of: RSC advances. Volume 8:Issue 54(2018)
• Page Start: 30761
• Page End: 30776
• Publication Date: 2018-08-31
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8ra06676k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A practical, concise and straightforward total synthesis of kealiiquinone1, a naphtho[2, 3- d ]imidazole alkaloid obtained from the Micronesian marine sponge Leucetta sp. was accomplished. Abstract : A practical, concise and straightforward total synthesis of kealiiquinone1, 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.