title: Total synthesis of 7'-desmethylkealiiquinone.
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.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, United States.
authors.forename: Heather M
authors.initials: HM
authors.lastname: Lima
authors.forename: Rasapalli
authors.initials: R
authors.lastname: Sivappa
authors.forename: Muhammed
authors.initials: M
authors.lastname: Yousufuddin
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Lovely
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D003500:Cyclization; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008386:Marine Biology; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D011161:Porifera / Q000737:chemistry
chemical_list: C573424:7'-desmethylkealiiquinone; D000470:Alkaloids; D007093:Imidazoles; D009285:Naphthoquinones