ASYMMETRIC-SYNTHESIS OF 1-BENZYLTETRAHYDROISOQUINOLINES USING CHIRAL OXAZOLO[2,3-A]TETRAHYDROISOQUINOLINES

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 (1c; a bronchodilator).

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 39; no. 5; pp. 1126 - 1131
Main Authors HASHIGAKI, K, KAN, K, QAIS, N, TAKEUCHI, Y, YAMATO, M
Format Journal Article
LanguageEnglish
Published TOKYO Pharmaceutical Soc Japan 1991
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
PHENYLGLYCINOL
1-CHLOROISOCHROMAN
ALKYLATION
(S)-TETRAHYDROPAPAVERINE
(S)-TRIMETOQUINOL
ISOQUINOLINE ALKALOIDS
OXAZOLO[2,3-A]TETRAHYDROISOQUINOLINE
ASYMMETRIC SYNTHESIS
1-BENZYLTETRAHYDROISOQUINOLINE
(S)-NORAMEPAVINE
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Summary: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 (1c; a bronchodilator).
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.39.1126