Studies on the Alkaloids of Menispermaceous Plants. CCVII

1 January 1964

journal article
Published by Pharmaceutical Society of Japan in YAKUGAKU ZASSHI

Vol. 84 (10) , 1027-1029
https://doi.org/10.1248/yakushi1947.84.10_1027

Abstract

Following the previous work on the synthesis of the antipode of isotrilobine (VI) from the antipode (N-methyl-dihydroepistephanine-B) of O-methylrepandine (II), O-methylanhydrodemethylrepandine (VI) was synthesized from repandine (III), obtained by the treatment of oxyacanthine (I) with dilute hydrochloric acid, by demethylation with hydrogen bromide in acetic acid solution, dehydrative cyclization with saturated aqueous solution of hydrogen bromide, and subsequent O-methylation. The infrared spectrum (chloroform) of this free base (VI) was in complete agreement with that of natural isotrilobine. Its picrate of m. p. 188-190°, [α]_D¹⁴+200° (Me₂CO), was identified with isotrilobine picrate through infrared spectrum (KBr) (cf. Table I).

Keywords

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