Stereoselective synthesis of the two trans-(16-hydroxymethyl)-3-methoxy-13α-estra-1,3,5(10)-trien-17-ol isomers

Erzsébet Mernyák, János Wölfling, Gábor Bunkóczi, Lingfei Luo, Thomas R. Schneider, Gyula Schneider

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Abstract

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.

Original languageEnglish
Pages (from-to)1141-1148
Number of pages8
JournalCollection of Czechoslovak Chemical Communications
Volume68
Issue number6
DOIs
Publication statusPublished - Jun 1 2003

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Keywords

  • 13α-Estrones
  • Claisen condensation
  • Cyclic acetals
  • Diols
  • NMR spectroscopy
  • Stereoselective reduction
  • Steroids
  • X-Ray diffraction

ASJC Scopus subject areas

  • Chemistry(all)

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