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Paper | Regular issue | Vol 45, No. 6, 1997, pp.1111-1119
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7782
Asymmetric Synthesis of (S)-1-(5-Hydroxy-2-methoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (So-called "Dehassiline")

Keiko Takaba, Jun Haginaka, Jun-ichi Kunitomo,* and Tetsuro Shingu

*Faculty of Pharmaceutical Science, Mukogawa-Women's University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan

Abstract

Optically active, (S)-1-(5-hydroxy-2-methoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (so-called "dehassiline") (1) was synthesized via highly stereoselctive reduction of the 3,4-dihydroisoquinolinium ion possessing a chiral auxiliary by Polniaszek’s method. The synthetic compound (1) was shown to be different from natural dehassiline, the structure of which should be revised.