Highly Selective Intramolecular Heterocyclization and Its Application to Synthesis of Biologically Active Compounds

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  • 高選択的なヘテロ環化反応の開発と生物活性物質の合成への応用
  • コウ センタクテキ ナ ヘテロ カンカ ハンノウ ノ カイハツ ト セイブツ

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Abstract

Progress toward highly selective intramolecular heterocyclization and its application to the syntheses of biologically active compounds have been reviewed. The highly selective electrophilic heteroatom nucleophiles cyclization of carbon-carbon π-bonds such as iodoiminothiolactonization, iodolactamization, amidomercuration, iodolactonization, and oxylactonization has been developed. Our recent advances taking advantage of stereoselective heterocyclization of homochiral substrates readily available from optical active amine, the Katsuki-Sharpless oxidation, lipase-mediated transesterification, and α-amino acids have provided an attractive entry into the functionalized heterocycles as chiral building blocks. A promising approach to the chiral synthesis of a number of biologically active compounds such as alkaloids, antibiotics, and pheromones has emerged.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 113 (11), 737-759, 1993

    The Pharmaceutical Society of Japan

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