Condensed Heteroaromatic Ring Systems. IX. Total Synthesis of Aaptamine

Takao Sakamoto, Norio Miura, Yoshinori Kondo, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

A five-step synthesis of aaptamine, a marine alkaloid containing a benzo[d,e][l,6]naphthy-ridine ring, from 6,7-dimethoxy-8-nitro-l(2H)-isoquinolone was accomplished in satisfactory yield. As a basis for the above synthesis, a facile preparation of 6,7-dimethoxy-l(2H)-isoquinolones from 3,4-dimethoxybenzaldehydes was developed using the palladium-catalyzed reaction of o-bromo-benzaldehyde derivatives with trimethylsilylacetylene as a key reaction.

Original languageEnglish
Pages (from-to)2760-2765
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume34
Issue number7
DOIs
Publication statusPublished - 1986 Jan 1

Keywords

  • 6,7-dimethoxy-1 (2H)-isoquinolone
  • aaptamine
  • palladium-catalyzed reaction
  • synthesis
  • trimethylsilylacetylene

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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