川骨成分の研究 第7報

Anhydronupharanediolの構造研究

抄録

Reduction product of desoxynupharidine was submitted to repeated exhaustive methylation and reduction and the nitrogen-free product (I), C₁₅H₃₀O, was named anhydronupharanediol. Oxidation of (I) with chromium trioxide yielded a lactone compound, C₁₅H₂₈O₂, and the same oxidation of the methyl ester (VI) of hydroxy acid yielded isocaproic acid and a dibasic acid (IX), C₁₅H₂₈O₄. The anhydride (X) of (IX) gave the diol (VII) by the action of lithium aluminum hydride and (VII) was derived to (I) with sulfuric acid. The zinc dust distillation product of the imide of (X) gave positive Ehrlich reaction. It was concluded from the foregoing results that the ether ring in (I) is five-membered and that the carbon atoms on both sides of ether oxygen are methylenes. On these basis, the structural formula for desoxynupharidine proposed earlier by the writers is withdrawn.