1963 年 83 巻 4 号 p. 394-398
Ponndorf and Bouveault-Blanc reductions of 6-keto group of dihydrothebainone (VI) and its 4-methyl ether were carried out. The production ratio of the resulting 6-OH-isomers was compared with those of 6-OH-isomers obtained by the same reduction of dihydrocodeinone (III) possessing 4, 5-ether ring. On Ponndorf reduction, also in 14-H-series the orientation of 6-hydroxy group of the main product i.e. alcohol was opposite with respect to the presence or absence of 4, 5-ether ring. These results are identical with those of 14-OH-series.