Studies on the Alkaloids of Menispermaceous Plants (Masao Tomita). LXXXIII On the Structure of Biscoclaurine Alkaloids. (4). Cleavage of Cycleanine by Metallic Sodium in Liquid Ammonia

Eiichi Fujita; Fujio Murai

doi:10.1248/yakushi1947.71.10_1043

YAKUGAKU ZASSHI

Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903

Studies on the Alkaloids of Menispermaceous Plants (Masao Tomita). LXXXIII

On the Structure of Biscoclaurine Alkaloids. (4). Cleavage of Cycleanine by Metallic Sodium in Liquid Ammonia

Eiichi Fujita, Fujio Murai

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1951 Volume 71 Issue 10 Pages 1043-1046

DOI https://doi.org/10.1248/yakushi1947.71.10_1043

[Correction] Journal of the Pharmaceutical Society of Nippon Vol.71 No.12 (1951) pp.e6ad-e6ad

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Abstract

When cycleanine (I) is reacted with metallic sodium in liquid ammonia, it is bisected into l-1-(4′-hydroxybenzyl)-6, 7-dimethoxyl-N-methyl-1, 2, 3, 4-tetrahydroisoquinoline (l-armepavine) (II). Therefore, it has been confirmed that the structure of cycleanine and the steric configuration of the two asymmetric centers in the molecule must be represented by (I).

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