Collect. Czech. Chem. Commun. 2003, 68, 1141-1148

Stereoselective Synthesis of the Two trans-(16-Hydroxymethyl)-3-methoxy-13α-estra-1,3,5(10)-trien-17-ol Isomers

Erzsébet Mernyáka, János Wölflinga, Gábor Bunkóczib, Lingfei Luob, Thomas R. Schneiderb and Gyula Schneidera,*

a Department of Organic Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary
b Institute of Inorganic Chemistry, University of Göttingen, Tammannstr. 4, D-37077 Göttingen, Germany


Reduction of 16-(hydroxymethylidene)-3-methoxy-13α-estra-1,3,5(10)-trien-17-one yielded a mixture of two diastereomeric diols in the 6:1 ratio. The configurations of the newly formed stereogenic centres were determined by X-ray crystallography and NMR spectroscopy (NOE experiments) on the compounds in their cyclic acetaldehyde acetal forms.

Keywords: Steroids; 13α-Estrones; X-Ray diffraction; NMR spectroscopy; Stereoselective reduction; Diols; Cyclic acetals; Claisen condensation.

References: 11 live references.