Total synthesis of 7'-desmethylkealiiquinone |
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Authors: | Lima Heather M Sivappa Rasapalli Yousufuddin Muhammed Lovely Carl J |
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Institution: | Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, United States. |
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Abstract: | The total synthesis of an analogue of the marine alkaloid kealiiquinone has been completed through application of an intramolecular Diels-Alder reaction of an imidazole-containing enyne. Oxidative aromatization of the lactone adduct and N-methylation facilitates C2-oxidation via the imidazolium salt. Conversion of the lactone to the phthalaldehyde derivative and then to the dihydroxybenzoquinone was achieved via a reaction with glyoxal in the presence of KCN. Esterification of the vinylogous diacid and deprotection provided 7'-desmethylkealiiquinone. |
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