Studies on the Synthesis of Hypotensive Compounds. II. : The Synthesis of Decahydroisoquinoline Derivatives

Abstract

Relating to the structure of reserpine, new aroyl derivatives of 2-methyl-and 2-ethyl-decahydro-7-isoquinolinols were synthesized as the quaternary ammonium salts. Hypotensive activity of these compounds are shown in Table I and II. 2-Methyldecahydro-7-isoquinolinol derivative was separated into the corresponding two stereoisomers (X-A and -B), while the 2-ethyldecahydro-7-isoquinolinol derivative yielded four stereoisomers (IV-B₁, -B₂, -C, -D). It was clarified that two stereoisomers of 2-methyldecahydro-7-isoquinolinol possess cis configuration at the ring juncture, the four stereoisomers obtained from 2-ethyldecahydro-7-isoquinolinol derivatives, one pair (IV-B₁, -C) possesses cis configuration and the other (IV-B₂, -D), trans configuration.