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Paper | Regular issue | Vol 43, No. 8, 1996, pp.1777-1786
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7540
■ Asymmetric Synthesis of (R)-1-(2-Methoxy-3,4-methylenedioxybenzyl)-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoqunoline (So-called "Fumarizine")

Keiko Takaba, Keiko Komori, Jun-ichi Kunitomo,* and Toshimasa Ishida

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

Abstract

(R)-1-(2-Methoxy-3,4-methylenedioxybenzyl)-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (so-called "fumarizine") (1) was synthesized via the stereoselective reduction of the corresponding chiral iminium ion (11), which was obtained by the Bischler-Napieralski cyclization of N-[(R)-1-phenylethyl]-N-2-(3,4-methylenedioxyphentlethyl]-2-(2-methoxy-3,4-methylenedioxyphenyl)acetamide (10). The synthetic compound (1) was shown to difffer from natural fumarizine, the structure of which is not formula (1).