Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core

Three analogues of 1α,25-dihydroxyvitamin D(3) (calcitriol), featuring a trans-fused decalin C,D-core with local S(2)-symmetry, and possessing identical side-chain and seco-B,A-ring structures, have been synthesized starting from readily available (4aR,8aS)-octahydronaphthalene-1,5-dione (7). The ve...

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Detalles Bibliográficos
Autores principales: Minne, Garrett, Verlinden, Lieve, Verstuyf, Annemieke, De Clercq, Pierre J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254054/
https://www.ncbi.nlm.nih.gov/pubmed/19255548
http://dx.doi.org/10.3390/molecules14020894
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author Minne, Garrett
Verlinden, Lieve
Verstuyf, Annemieke
De Clercq, Pierre J.
author_facet Minne, Garrett
Verlinden, Lieve
Verstuyf, Annemieke
De Clercq, Pierre J.
author_sort Minne, Garrett
collection PubMed
description Three analogues of 1α,25-dihydroxyvitamin D(3) (calcitriol), featuring a trans-fused decalin C,D-core with local S(2)-symmetry, and possessing identical side-chain and seco-B,A-ring structures, have been synthesized starting from readily available (4aR,8aS)-octahydronaphthalene-1,5-dione (7). The very short sequences involve the simultaneous introduction of the side-chain and seco-B,A-ring fragments via Suzuki and Sonogashira coupling reactions. The analogues are devoid of relevant biological activity.
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spelling pubmed-62540542018-11-30 Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core Minne, Garrett Verlinden, Lieve Verstuyf, Annemieke De Clercq, Pierre J. Molecules Article Three analogues of 1α,25-dihydroxyvitamin D(3) (calcitriol), featuring a trans-fused decalin C,D-core with local S(2)-symmetry, and possessing identical side-chain and seco-B,A-ring structures, have been synthesized starting from readily available (4aR,8aS)-octahydronaphthalene-1,5-dione (7). The very short sequences involve the simultaneous introduction of the side-chain and seco-B,A-ring fragments via Suzuki and Sonogashira coupling reactions. The analogues are devoid of relevant biological activity. Molecular Diversity Preservation International 2009-02-24 /pmc/articles/PMC6254054/ /pubmed/19255548 http://dx.doi.org/10.3390/molecules14020894 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Minne, Garrett
Verlinden, Lieve
Verstuyf, Annemieke
De Clercq, Pierre J.
Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core
title Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core
title_full Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core
title_fullStr Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core
title_full_unstemmed Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core
title_short Synthesis of 1α,25-Dihydroxyvitamin D Analogues Featuring a S(2)-symmetric CD-ring Core
title_sort synthesis of 1α,25-dihydroxyvitamin d analogues featuring a s(2)-symmetric cd-ring core
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254054/
https://www.ncbi.nlm.nih.gov/pubmed/19255548
http://dx.doi.org/10.3390/molecules14020894
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