4,4-Dimethyl-5α-androstan-2-one and lupan-2-one, preapared from the 3-ketones by general methods for transposing oxo-groups, undergo substitutions at position 3. Acetoxylation and bromination proceed easily and introduce 3α-substituents; formylation to the 3-hydroxymethylene-2-ketones is difficult and gives poor yields even under forcing conditions.
A. D. Boul, R. Macrae and G. D. Meakins, J. Chem. Soc., Perkin Trans. 1, 1974, 1138 DOI: 10.1039/P19740001138
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