Synthesis of dragmacidin D via direct C-H couplings

Debashis Mandal, Atsushi D. Yamaguchi, Junichiro Yamaguchi*, Kenichiro Itami

*この研究の対応する著者

研究成果: Article査読

124 被引用数 (Scopus)

抄録

Dragmacidin D, an emerging biologically active marine natural product, has attracted attention as a lead compound for treating Parkinson's and Alzheimer's diseases. Prominent structural features of this compound are the two indole-pyrazinone bonds and the presence of a polar aminoimidazole unit. We have established a concise total synthesis of dragmacidin D using direct C-H coupling reactions. Methodological developments include (i) Pd-catalyzed thiophene-indole C-H/C-I coupling, (ii) Pd-catalyzed indole-pyrazine N-oxide C-H/C-H coupling, and (iii) acid-catalyzed indole-pyrazinone C-H/C-H coupling. These regioselective catalytic C-H couplings enabled us to rapidly assemble simple building blocks to construct the core structure of dragmacidin D in a step-economical fashion.

本文言語English
ページ(範囲)19660-19663
ページ数4
ジャーナルJournal of the American Chemical Society
133
49
DOI
出版ステータスPublished - 2011 12 14
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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