Stereoselective synthesis of 25S,26-dihydroxyvitamin D3

•A convergent synthesis of 25S,26-dihydroxyvitamin D3 was achieved for biological testing.•An efficient and versatile synthetic approach to the all isomers of 25,26-dihydroxyvitamin D3 was established by osmium catalyzed asymmetric dihydroxylation.•The construction/formation of the triene moiety/sys...

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Bibliographic Details
Published inThe Journal of steroid biochemistry and molecular biology Vol. 177; pp. 247 - 249
Main Authors Sigüeiro, Rita, González-Berdullas, Patricia, Loureiro, Julian, Mouriño, Antonio, Maestro, Miguel A.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 01.03.2018
Subjects
25S,26-Dihydroxyvitamin D3
Synthesis
Vitamin D3 metabolites
25S,26-Dihydroxyvitamin D3
Vitamin D3 metabolites
Synthesis
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Summary:•A convergent synthesis of 25S,26-dihydroxyvitamin D3 was achieved for biological testing.•An efficient and versatile synthetic approach to the all isomers of 25,26-dihydroxyvitamin D3 was established by osmium catalyzed asymmetric dihydroxylation.•The construction/formation of the triene moiety/system was done by the Wittig-Horner approach. A convergent approach to 25S,26-dihydroxyvitamin D3 (1) has been developed in our laboratories. The A-ring and the CD-fragment are constructed from ergocalciferol and Inhoffen-Lythgoe diol, respectively. The triene system is assembled by a Wittig-Horner coupling. With this convergent synthesis, a novel hydroxylated vitamin D metabolite in our laboratory is available for biological testing.
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content type line 23
ISSN:0960-0760
1879-1220
DOI:10.1016/j.jsbmb.2017.07.016