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

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Title:Stereoselective Synthesis of the Two trans-(16-Hydroxymethyl)-3-methoxy-13α-estra-1,3,5(10)-trien-17-ol Isomers
Creators:
Mernyák, Erzsébet
Wölfling, János
Bunkóczi, Gábor
Luo, Lingfei
Schneider, Thomas R.
Schneider, Gyula
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 6, pp. 1141-1148
Uncontrolled Keywords:Stereoselective reduction, 13α-Estrones, Claisen condensation, X-Ray diffraction, Steroids, Diols, Cyclic acetals, NMR spectroscopy

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. <p>

Title:Stereoselective Synthesis of the Two trans-(16-Hydroxymethyl)-3-methoxy-13α-estra-1,3,5(10)-trien-17-ol Isomers
Creators:
Mernyák, Erzsébet
Wölfling, János
Bunkóczi, Gábor
Luo, Lingfei
Schneider, Thomas R.
Schneider, Gyula
Uncontrolled Keywords:Stereoselective reduction, 13α-Estrones, Claisen condensation, X-Ray diffraction, Steroids, Diols, Cyclic acetals, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:6
Page Range:pp. 1141-1148
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031141UNSPECIFIED
ID Code:2110
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Mernyák, Erzsébet; Wölfling, János; Bunkóczi, Gábor; Luo, Lingfei; Schneider, Thomas R.; Schneider, Gyula (2003) Stereoselective Synthesis of the Two trans-(16-Hydroxymethyl)-3-methoxy-13α-estra-1,3,5(10)-trien-17-ol Isomers. Collection of Czechoslovak Chemical Communications, 68 (6). pp. 1141-1148. ISSN 0010-0765

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