
%0 Journal Article
%A Collins, DJ 
%A Hobbs, JJ 
%A Rawson, RJ 
%T 4,5-Seco-4,6-cyclosteroids. II. Synthesis of 4,5-Seco-4,6-cyclo-6&#946;-cholestan-5&#945;-ol
%J Australian Journal of Chemistry
%D 1969/03/01
%V 22
%N 3
%P 627-635
%K 
%R https://doi.org/10.1071/CH9690627
%U https://www.publish.csiro.au/paper/CH9690627 
%X 5-oxo-4,5-secocholestan-4-oic acid methyl ester (XIIIb) was converted into the corresponding cyclic ethylene acetal (XIVb) which, upon successive reduction with lithium aluminium hydride and acid hydrolysis, gave 4-hydroxy-4,5-secochol-estan-5-one (XVa), converted into the tosyl ester (XVb). Base-catalysed intra-molecular alkylation of the latter gave mainly A-homo-4a-oxacholest-5-ene (XVII), together with 4,5-seco-4,6-cyclo-6&#946;-cholestan-5-one (IIIc), reduced with lithium aluminium hydride to 4,5-seco--1,6-cyclo-6&#946;-cholestan-5&#945;-ol (IIb). This was identical with material previously prepared by transformation of 4,5-seco-4,6-cyclo-6&#946;-cholestane-3&#946;,5&#945;-diol (IIa), obtained from reductive rearrangement of 6&#946;-bromo-4&#946;,5-epoxy-5,&#946;-cholestan-3&#946;-ol (I).     Some other approaches to the synthesis of 4,5-seco-4,6-cyolo-6&#946;- cholestane derivatives are described. 
