期刊
TETRAHEDRON
卷 56, 期 37, 页码 7217-7228出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(00)00646-3
关键词
radicals and radical reactions; cyclisation; alkaloids; enamides
Novel radical cyclisation reactions, mediated by tributyltin hydride, samarium(II) iodide or manganese(III) acetate, have been explored to form tri- and tetra-cyclic ring systems related to the Amaryllidaceae or Erythrina family of alkaloids. Haloethanamide precursors possessing a cyclohexenone ring have been shown to form octahydroindolones, and erythrinane-type systems can be formed from precursors bearing unsaturated side-chains in tandem cyclisations. An octahydroindolone has been converted to the ring skeleton of gamma-lycorane using samarium(II) iodide while reaction with manganese(III) acetate has been shown to yield a novel tetracyclic ring system bearing a 7-membered ring. Finally, a new tandem cyclisation of a cyclohexenone aryl halide has been shown to provide a quick approach to a 5,5,6,6-tetracycle related to erythrinane natural products. (C) 2000 Elsevier Science Ltd. All rights reserved.
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