Abstract:
Treatment of the gem-cyano ethoxycarbonyl compounds 1a-c with NaBH4 in 2-propanol or PEG-400
produced reduction of the ethoxycarbonyl group and simultaneous reductive deacetoxylation. Similar treatment of 7 with
NaBH4-CoCl2 produced selective reductuion of the cyano group to aminomethyl group and rearrangement O ® N of an
acetyl group to aminomethyl group. Treatment of 1a-c and 7 with LiAlH4 gave, after acetylation, the
gem-aminomethyl-hydroxymethyl compound 6a-c and 11 respectvely. Compounds 4a-b, 5a-b and 6a-b show a prefered
conformations with both acetoxy groups in a equatorial disposition. However compounds 4c, 5c and 6cprefer the
conformation with both acetoxy groups in an axial disposition.