6-Endo-Trig Mode Cyclization to a Hydrindanone Using Samarium (II) Iodide

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  • SONO Masakazu
    <i>Faculty of Pharmaceutical Sciences, Tokushima Bunri University</i>

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Other Title
  • ヨウ化サマリウムを用いた6-Endo-Trig 型の環化反応によるヒドリンダノン類縁体の合成
  • ヨウカ サマリウム オ モチイタ 6 Endo Trigガタ ノ カンカ ハンノウ ニ ヨル ヒドリンダノン ルイエンタイ ノ ゴウセイ

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Abstract

Samarium(II) iodide has been employed to promote the vinylogous pinacol coupling reaction of aldehyde to α, β-unsaturated ketones. The diastereoselectivity of 6-endo-trig mode products was changed by the addition of a proton source and/or HMPA and by the reaction temperature. The stereochemistry of the hydrindanone was controlled by the coordinated samarium species, resulting in the cis-orientation in respect of the hydroxyl group at C-4 and the juncture proton at C-3a under mild reaction conditions. Coronafacic acid has been synthesized from a hydrindanone prepared by the cyclization reaction of the enone-aldehyde with samarium(II) iodide.<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 123 (8), 653-663, 2003-08-01

    The Pharmaceutical Society of Japan

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