ArticleThe Journal of organic chemistry2014
Total synthesis of 7'-desmethylkealiiquinone, 4'-desmethoxykealiiquinone, and 2-deoxykealiiquinone.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed, 25 citations in OpenAlex.
- Room Temperature Diels-Alder Reactions of 4-Vinylimidazoles.Molecules (Basel, Switzerland) · 2024Article
- Total synthesis of kealiiquinone: the regio-controlled strategy for accessing its 1-methyl-4-arylbenzimidazolone core.RSC advances · 2018Article
- Total synthesis and cytotoxicity of Leucetta alkaloids.Bioorganic & medicinal chemistry · 2017Article
- Studies Towards theEuropean journal of organic chemistry · 2015Article
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Authors and funding
4 authors at 1 institution in 1 country.
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Abstract
Synthetic approaches to the imidazonaphthoquinone core of kealiiquinone and related Leucetta-derived alkaloids are described. The polysubstituted benzimidazole framework can be constructed through intramolecular Diels-Alder reactions of propiolate-derived enynes followed by oxidation. Adjustment of the oxidation state of the thus formed lactone allows introduction of the 2,3-dihydroxybenzoquinone moiety through a presumed benzoin-like condensation between a phthaldehyde derivative and a masked glyoxal equivalent catalyzed by a cyanide ion. Oxidation of the C2-position can be accomplished through application of an operationally simple treatment of an imidazolium salt with bleach, thus producing the corresponding 2-imidazolone. Debenzylation of a late stage intermediate en route to kealiiquinone was compromised by concomitant O-demethylation upon treatment with triflic acid resulting in the formation of non-natural 7'-desmethylkealiiquinone. Other endgame strategies were evaluated; however, these efforts did not lead to completion of a synthesis of kealiiquinone but did provide access to other closely related analogues.
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