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Note | Regular issue | Vol 48, No. 8, 1998, pp.1623-1630
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8168
Asymmetric Synthesis of So-called "Dehassiline" Isomer, (S)-1-(2'-Hydroxy-5'-methoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

Akiko Watanabe and Jun-ichi Kunitomo*

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

Abstract

A so-called "dehassiline" isomer, (S)-1-(2’-hydroxy-5’-methoxybenzyl)-7-hydroxy-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1) was asymmetrically synthesized via the stereoselective reduction with
sodium borohydride at -78 °C of the corresponding 3,4-dihydroisoquinolinium ion possessing a chiral auxiliary. The spectral data for the synthetic compound (1) differed from those reported for natural dehassiline, the structure of which must be reexamined.