Studies toward the total synthesis of axinellamine and massadine |
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Authors: | Sivappa Rasapalli Hernandez Nora M He Yong Lovely Carl J |
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Affiliation: | Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, Texas 76019, USA. |
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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. |
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