Studies on tetrahydroisoquinolines. XXVI. A biomimetic synthesis of 5-oxygenated 1,2,3,4-tetrahydroisoquinolines.

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1986 English Publisher:Pharmaceutical Society of JapanJournal:Chemical and Pharmaceutical Bulletin, volume 34, pages 66-70 (issn: 0009-2363, eissn: 1347-5223,

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Authors: HARA, HIROSHI; TSUNASHIMA, AKIRA; SHINOKI, HIROSHI; AKIBA, TOSHIFUMI; HOSHINO, OSAMU; UMEZAWA, BUNSUKE;

doi: 10.1248/cpb.34.66

Studies on tetrahydroisoquinolines. XXVI. A biomimetic synthesis of 5-oxygenated 1,2,3,4-tetrahydroisoquinolines.

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Abstract

Treatment with acetic anhydride-conc. sulufuric acid of o-quinol acetates (7, 11, 18, 19, 20, 28 and 34), which were derived from the corresponding 6-hydroxy-7-methoxytetrahydroisoquinolines (6, 12, 15, 16, 17, 27 and 31), gave the 5, 6-diacetates (8, 13, 21, 22, 23, 29 and 33, respectively). The diacetates were transformed into the corresponding 5, 6, 7-trimethoxytetrahydroisoquinolines (10, 14, 24, 25, 26, 30 and 32) by hydrolysis and subsequent methylation.

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University of Tokyo
Japan

Keywords

o-quinol acetate

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