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An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13α-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone...
A simple synthetic route has been developed for the synthesis of 16-halo-d-homosteroids in both the normal and 13-epiestrone series by the Lewis acid-catalyzed cyclization of an unsaturated secoestrone aldehyde and its 13α isomer.
16,17-seco-3-Methoxyestra-1,3,5(10),16-tetraen-17-al undergoes intramolecular nitrone 1,3-dipolar cycloaddition with both hydroxylamine and N-methylhydroxylamine to produce a single isoxazolidine isomer in each case. The ring-closures of the hydrazones and the aldazine derived from the secoaldehyde lead to fused N-containing heterocycles via Lewis acid-induced cyclization of the intermediate azomethine...
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