Condensed Heteroaromatic Ring Systems. V. Formal Synthesis of Matrine and Related Compounds Using Palladium-Catalyzed Carbon-Carbon Bond Formations as Key Reactions

Takao Sakamoto, Norio Miura, Yoshinori Kondo, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

The iodination and subsequent dehydroxychlorination of l,6-naphthyridin-5(6H)-one gave 5-chloro-8-iodo-1,6-naphthyridine, which was converted to the 5-methoxy derivative. Starting from this compound, didehydromatrine was synthesized by using palladium-catalyzed cross-coupling reactions with ethyl acrylate and 3-butyn-l-ol, as key reactions. Similarly, nordehydro-α-matrinidine was synthesized through four steps from 8-bromo-l,6-naphthyridine, obtained by the bromination of unsubstituted 1,6-naphthyridine.

Original languageEnglish
Pages (from-to)2018-2023
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume34
Issue number5
DOIs
Publication statusPublished - 1986 Jan 1

Keywords

  • 1,6-naphthyridine
  • 3-butyn-1-ol
  • didehydromatrine
  • ethyl acrylate
  • matrine
  • nordehydro-a-matrinidine
  • palladium-catalyzed reaction
  • synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Fingerprint Dive into the research topics of 'Condensed Heteroaromatic Ring Systems. V. Formal Synthesis of Matrine and Related Compounds Using Palladium-Catalyzed Carbon-Carbon Bond Formations as Key Reactions'. Together they form a unique fingerprint.

Cite this