Asymmetric Synthesis of 1-Benzyltetrahydroisoquinolines Using Chiral Oxazolo[2,3-a]tetrahydro-isoquinolines

Kuniko Hashigaki, Keizo Kan, Nazmul Qais, Yasuo Takeuchi, Masatoshi Yamato

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A novel synthetic route to enantiomerically pure 1-benzyltetrahydroisoquinolines (1) was developed via the reaction of oxazolo[2,3-a]tetrahydroisoquinoline (5) with benzyltriisopropoxytitanium compounds (10). This method was applied to the synthesis of (S)-trimetoquinol (lc; a bronchodilator).

Original languageEnglish
Pages (from-to)1126-1131
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume39
Issue number5
DOIs
Publication statusPublished - 1991

Keywords

  • (S)-norarmepavine (S')-tetrahydropapaverine (5)-trimetoquinol asymmetric synthesis
  • oxazolo[2,3-«]tetrahydroisoquinoline 1-benzyltetrahydroisoquinoline 1-chloroisochroman phenylglycinol

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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