1963 年 83 巻 4 号 p. 389-393
6-Keto group of 14-hydroxydihydrothebainone and its 4-methyl ether (V) was reduced with sodium borohydride, lithium aluminum hydride and by Ponndorf and Bouveault-Blanc procedure. The production ratios of the resulting isomers of alcohols (III and IV, VI and VIII) were investigated. The results obtained above were compared with those of the reduction of 4, 5-ether derivative (I) (Table I and Fig. 1). The orientation of 6-hydroxyl groups of newly prepared isomers (III, IV, VI and VII) were elucidated on the basis of the results of their ethoxycarbonylation (Fig. 2) and Oppenauer oxidation.