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Synlett 1991; 1991(6): 391-392
DOI: 10.1055/s-1991-20737
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Stereocontrolled Construction of B-Ring of Grayanotoxins via Samarium(II) Iodide Promoted Pinacol Coupling Cyclization

Toshiyuki Kan* , Fuyuhiko Matsuda, Mitsutoshi Yanagiya, Haruhisa Shirahama
  • *Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060, Japan
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Publication Date:
07 March 2002 (online)

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Stereocontrolled Cyclization of the 7-membered B-ring of grayanotoxins, main toxic substances in leaves of plants belonging to family Ericaceae, has been effectively achieved, employing a samarium(II) iodide mediated pinacol coupling reaction stereocontrolled by the nearby C-3 hydroxyl group.