1447920-38-8Relevant articles and documents
Synthesis of 2-ethyl-19-nor analogs of 1α,25-dihydroxyvitamin D 3
Laplace, Duchan R.,Van Overschelde, Michel,De Clercq, Pierre J.,Verstuyf, Annemieke,Winne, Johan M.
, p. 728 - 735 (2013)
The synthesis of two new A-ring precursors, useful for the convergent assembly of 2α-ethyl and 2β-ethyl derivatives of 19-nor-1α,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 2α-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. Two new phosphanone building blocks, useful for the stereocontrolled synthesis of 2-ethyl-substituted 19-nor analogs of 1α,25-dihydroxyvitamin D 3, were prepared from quinic acid. This route offers an attractive practical solution for the introduction of these synthetically challenging but highly interesting A-ring modifications. Copyright
