
%0 Journal Article
%A Blair, IA 
%A Frith, RG 
%A Phillipou, G 
%A Seaborn, CJ 
%T Regeneration of a Steroid C13 Angular Methyl Group from a Functionalized Precursor : Application to the Preparation of C 18-<sup>2</sup>H<sub>3</sub> Steroids and C 18-<sup>2</sup>H<sub>3</sub> D-Homosteroids
%J Australian Journal of Chemistry
%D 1979/10/01
%V 32
%N 10
%P 2327-2330
%K 
%R https://doi.org/10.1071/CH9792327
%U https://www.publish.csiro.au/paper/CH9792327 
%X 3&#946;-Acetoxypregn-5-eno-18,20-lactone has been converted into 3&#946;,20&#946;-dimethoxypregn-5-ene (6) by using electrochemical deoxygenation of a C13 formyl intermediate as a key reaction. The electrochemicalreduction is also shown to be applicable to multiple deuterium labelling of the C13 angular methyl group in high isotopic purity.A facile preparation of 3&#946; -hydroxy-17&#945;-methyl-D-homoandrost-5-en-17a-one (10) and its respective C18-2H3 analogue from the ether (6) is described. 
