title: Studies toward the total synthesis of axinellamine and massadine.
abstract: Intramolecular Diels-Alder reactions of several N-O linked 4-vinylimidazole dimers provide the expected adduct in moderate to good yield as a single, all trans stereoisomer, along with smaller amounts of the inverse electron demand adduct. Oxidative rearrangement of the cycloadducts occurs on treatment with Davis' reagent, providing a single spiro imidazolone in good yield and with excellent levels of stereocontrol albeit epimeric at the spiro center found in axinellamine and massadine.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA.
authors.forename: Rasapalli
authors.initials: R
authors.lastname: Sivappa
authors.forename: Nora M
authors.initials: NM
authors.lastname: Hernandez
authors.forename: Yong
authors.initials: Y
authors.lastname: He
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Lovely
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry