Synthesis of 2-Ethyl-19-nor Analogs of 1[alpha],25-Dihydroxyvitamin D3

The synthesis of two new A-ring precursors, useful for the convergent assembly of 2[alpha]-ethyl and 2[beta]-ethyl derivatives of 19-nor-1[alpha],25-dihydroxyvitamin D3, is described. These building blocks were prepared in 14 steps from quinic acid, which led to a new and practical synthesis of 2[al...

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Published inEuropean journal of organic chemistry Vol. 2013; no. 4; p. 728
Main Authors Laplace, Duchan R, Van Overschelde, Michel, De Clercq, Pierre J, Verstuyf, Annemieke, Winne, Johan M
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.02.2013
Subjects
Cells
Rodents
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Summary:The synthesis of two new A-ring precursors, useful for the convergent assembly of 2[alpha]-ethyl and 2[beta]-ethyl derivatives of 19-nor-1[alpha],25-dihydroxyvitamin D3, is described. These building blocks were prepared in 14 steps from quinic acid, which led to a new and practical synthesis of 2[alpha]-ethyl-14-epi-19-nor-20-epi-23-yne-1,25(OH)2D3, an analog that shows a remarkably low calcemic effect in mice, while retaining the ability to promote cell differentiation and to inhibit cell proliferation in a number of human cancer cell lines. [PUBLICATION ABSTRACT]
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201201261