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Synthesis and vitamin D receptor affinity of 16-oxa vitamin D3 analogues

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Abstract

Two novel 16-oxa-vitamin D3 analogues were synthesized using a tandem Ti(II)-mediated enyne cyclization/Cu-catalyzed allylation, Ru-catalyzed ring-closing metathesis reaction, and a low-valent titanium (LVT)-mediated stereoselective radical reduction of 8α,14α-epoxide as the key steps for the synthesis of the 16-oxa-C,D ring unit. The vitamin D receptor-binding affinity of the synthesized analogues, 16-oxa-1α,25-(OH)2VD3 and 16-oxa-19-nor-1α,25-(OH)2VD3, was evaluated by fluorescence polarization vitamin D receptor competitor assay and time-resolved fluorescence energy transfer vitamin D receptor co-activator assay.

Graphical abstract: Synthesis and vitamin D receptor affinity of 16-oxa vitamin D3 analogues

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Publication details

The article was received on 29 Oct 2019, accepted on 18 Nov 2019 and first published on 19 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02339A
Org. Biomol. Chem., 2019, Advance Article

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    Synthesis and vitamin D receptor affinity of 16-oxa vitamin D3 analogues

    K. Ibe, T. Yamada and S. Okamoto, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB02339A

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