Direct dehydrogenation of 18-norandrost-13-enes (1a and b) with selenium dioxide gave the corresponding 7α-hydroxy-18-norandrosta-8,11,13-trienes (2a and b) in one step. The corresponding 7α-acetates (2c and d) were obtained together with the epimeric 7β-acetates (9a and b) on treatment of the 18-norandrosta-7,13-dienes (8a and c) with mercury(II) acetate. The mechanisms for both aromatisation processes are discussed.
C. L. Hewett, S. G. Gibson, I. M. Gilbert, J. Redpath, D. S. Savage, T. Sleigh and R. Taylor, J. Chem. Soc., Perkin Trans. 1, 1975, 336 DOI: 10.1039/P19750000336
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