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Paper | Regular issue | Vol 51, No. 1, 1999, pp.119-129
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8372
A Synthesis of Some Trimethoxylated 1,2,3,4-Tetrahydroisoquinoline Alkaloids via Pummerer Reaction of N-Trimethoxybenzyl-N-[2-(phenyl-
sulfinyl)ethyl]formamides

Tatsumi Shinohara, Akira Takeda, Jun Toda, Michiyo Kohno, and Takehiro Sano*

*Showa Pharmaceutical University, 3-3165, Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract

Pummerer reaction of N-trimethoxybenzyl-N-[2-(phenylsulfinyl)ethyl]formamides (7) gave N-formyl-1,2,3,4-tetrahydro-4-phenyl-sulfanylisoquinolines (9) which were converted into trimethoxylated 1,2,3,4-tetrahydroisoquinoline alkaloids in the family of Cactaceae, formylanhalinine (10a), nortehaunine (12a), anhalinine (12b), and tehaunine (13a).