防已科植物アルカロイド研究 (第192報)

数種のBiscoclaurine型第四級塩基に対するLiAlH₄の作用

抄録

A production of tertiary base has been investigated by the reaction of excess LiAlH₄ in dehydrated tetrahydrofuran with non-phenolic quaternary base, dl-laudanosine (III) methiodide, O, O-dimethylcorytuberine (IV) methiodide and dl-canadine (V) methiodide, and with biscoclaurine-type non-phenolic quaternary base, O-methyldauricine (VI) dimethiodide, isotetrandrine (VII) dimethiodide and insularine (VIII) dimethiodide, applying the Cope method.
Methiodide of (III), (IV) and (V), having comparatively simpler structure, gave the corresponding tertiary base in better yields, however, only a few amount of desired tertiary base was produced from biscoclaurine-type base of being rather complicated in its structure. On the other hand, the reaction of aporphine type, phenolic quaternary base, corytuberine (X) methiodide and isocorydine (XI) methiodide, ended in almost complete recovery of the starting material.