
%0 Journal Article
%A Ferro, V 
%A Skelton, BW 
%A Stick, RV 
%A White, AH 
%T The Synthesis of Some Pyrrolidines as Potential Precursors to Retronecine
%J Australian Journal of Chemistry
%D 1993/06/01
%V 46
%N 6
%P 787-803
%K 
%R https://doi.org/10.1071/CH9930787
%U https://www.publish.csiro.au/paper/CH9930787 
%X Methyl &#946;-D-galactopyranoside was converted into methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-&#946;-D-arabino-hexoside, but subsequent transformation of the anomeric centre into a dithioacetal was unsatisfactory. Alternatively, methyl &#946;-D- galactopyranoside easily gave methyl 4-azido-3,6-di-O-benzyl-2,4-dideoxy-&#946;-D-arabino-hexoside, and this could be transformed by a reductive amination into two pyrrolidines as potential precursors to retronecine. Related chemistry gave (4S,5S,6R)-6-benzyloxy-4-benzyloxymethyl-3-oxa-1-azabicyclo[3.3.0]octan-2-one, the structure of which was confirmed by a single-crystal X-ray structure determination. Finally, the synthesis of a potential precursor to heliotridine (an epimer of retronecine ), namely methyl 4-azido-3-O-benzyl-6-O-t-butyldiphenylsilyl-2,4-dideoxy-&#945;-D-ribo-hexoside, from methyl &#945;-D- mannopyranoside is reported. 
