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

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

doi:10.1248/cpb.39.1126

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 journal › Article › peer-review

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 language	English
Pages (from-to)	1126-1131
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	39
Issue number	5
DOIs	https://doi.org/10.1248/cpb.39.1126
Publication status	Published - 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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10.1248/cpb.39.1126

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

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).",

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author = "Kuniko Hashigaki and Keizo Kan and Nazmul Qais and Yasuo Takeuchi and Masatoshi Yamato",

year = "1991",

doi = "10.1248/cpb.39.1126",

language = "English",

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pages = "1126--1131",

journal = "Chemical and Pharmaceutical Bulletin",

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T1 - Asymmetric Synthesis of 1-Benzyltetrahydroisoquinolines Using Chiral Oxazolo[2,3-a]tetrahydro-isoquinolines

AU - Hashigaki, Kuniko

AU - Kan, Keizo

AU - Qais, Nazmul

AU - Takeuchi, Yasuo

AU - Yamato, Masatoshi

PY - 1991

Y1 - 1991

N2 - 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).

AB - 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).

KW - (S)-norarmepavine (S')-tetrahydropapaverine (5)-trimetoquinol asymmetric synthesis

KW - oxazolo[2,3-«]tetrahydroisoquinoline 1-benzyltetrahydroisoquinoline 1-chloroisochroman phenylglycinol

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VL - 39

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EP - 1131

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 5

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

Abstract

Keywords

ASJC Scopus subject areas

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