Alkoxycarbonylmethylation of (3R, 10bS)-3-Phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline

Yasuo Takeuchi, Yoshio Kamada, Koji Nishimura, Hiromi Nishioka, Masayo Nishikawa, Kuniko Hashigaki, Masatoshi Yamato, Takashi Harayama

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

As part of a series of studies on synthesis of chiral 1-alkyltetrahydroisoquinolines, asymmetric synthesis of 1-alkoxycarbonylmethyl-l,2,3,4-tetrahydroisoquinoline (IV) was investigated. Two synthetic approaches using intermolecular and intramolecular Reformatsky-type reactions from (3R,10bS)-3-phenyl-2,3,5,6-tetrahydro-10bH-oxazolo[2,3-a]isoquinoline (1) were attempted, but high stereoselectivity could not be obtained. For the purpose of determining the absolute structures of the compounds (2, 3) obtained by the Reformatsky-type reactions, transformation of 3a to a chiral 1,3,4,6,7,11b-hexahvdro-2H-benzo[a]quinolizine (14) was investigated.

Original languageEnglish
Pages (from-to)796-801
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume42
Issue number4
DOIs
Publication statusPublished - Jan 1 1994

Keywords

  • Reformatsky reaction
  • alkoxycarbonylmethylation
  • asymmetric synthesis
  • benzo[a]quinolizine
  • diastereoselective alkylation
  • oxazolo[2,3-a]isoquinoline

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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