Construction of N-heterocycles fused with a highly substituted benzene ring by a benzyne-mediated cyclization/functionalization cascade reaction and its application to the total synthesis of marine natural products

研究成果: Review article査読

抄録

This account summarizes the development of a benzyne-mediated cyclization/functionalization protocol for the versatile construction of highly substituted benzene derivatives fused with an N-heterocyclic ring such as indolines, indoles, and related nitrogen-containing heterocycles. The protocol comprises sequential reactions initiated by generating a benzyne species and subsequent cyclization via addition of magnesium amide to the benzyne, followed by trapping of the resultant magnesium compound in situ with various electrophiles. The substituent scope was expanded by conducting a transmetalation on a copper species to introduce alkyl, aryl, and alkenyl substituents. The utility of the sequential reaction was demonstrated in the synthesis of a carbazole natural product (heptaphylline), pyrrolo[4,3,2-de]quinoline alkaloids (batzellines), and pyrrolo[2,3-c]carbazole alkaloids (dictyodendrines).

本文言語English
ページ(範囲)707-716
ページ数10
ジャーナルChemical and Pharmaceutical Bulletin
69
8
DOI
出版ステータスPublished - 2021 8 1

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

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