1979 年 27 巻 4 号 p. 953-962
Reduction of α-ketol acetates (5, 6, 7, and 8) of 5α-santanolide with NaBH4 and LiAlH (OBut)3 were investigated. The structure of diol monoacetates (9-16) was determined by means of spectroscopic methods and some chemical transformation reactions, oxidation and acetylation. Their conformations are discussed from their NMR data. O, O-Acyl rearrangement was observed in the NaBH4 reduction of α-ketol acetates (5, 6, and 8). The acid-and base-catalyzed O, O-acyl rearrangements of diol monoacetates (9-16) were also investigated. The acyl migration mechanisms are proposed.