Development of Boomerang-Type Intramolecular Cascade Reactions and Application to Natural Product Synthesis

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  • TAKASU Kiyosei
    Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University

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  • ブーメラン型分子内連続反応の精密制御と生理活性物質合成への応用
  • ブーメランガタ ブンシ ナイ レンゾク ハンノウ ノ セイミツ セイギョ ト セイリ カッセイ ブッシツ ゴウセイ エ ノ オウヨウ

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Abstract

Intramolecular cascade reaction has received much attention as a powerful methodology to construct a polycyclic framework in organic synthesis. We have been developing “boomerang-type cascade reaction” to construct a variety of polycyclic skeletons efficiently. In the above reactions, a nucleophilic function of substrates changes the character into an electrophile after the initial reaction, and the electrophilic group acts as a nucleophile in the second reaction. That is, the reaction center stepwise moves from one functional group back to the same one via other functional groups. The stream of the electron concerning the cascade reaction is like a locus of boomerang. We show here three different boomerang-type reactions via ionic species or free radicals. 1) Diastereoselective Michael-aldol reaction based on the chiral auxiliary method and enantioselective Michael-aldol reaction by the use of external chiral sources. 2) Short and efficient total syntheses of longifolane sesquiterpenes utilizing intramolecular double Michael addition as a key step. 3) Development of boomerang-type radical cascade reaction of halopolyenes to construct terpenoid skeletons and its regioselectivity.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 121 (12), 887-898, 2001-12-01

    The Pharmaceutical Society of Japan

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