The Michael addition of nucleophiles to the enzyme inhibitor 5,10-seco-oestra-4,5-diene-3,10,17-trione (2) gives 5,10-seco-oestr-5-ene derivatives (3) or A-homo-B-noroestr-4-ene derivatives (4) depending on the nucleophile.
D. F. Covey, K. A. Albert and C. H. Robinson, J. Chem. Soc., Chem. Commun., 1979, 795 DOI: 10.1039/C39790000795
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