96685-53-9Relevant articles and documents
Asymmetric Synthesis of Vitamin D3 Analogues: Organocatalytic Desymmetrization Approach toward the A-Ring Precursor of Calcifediol
Wang, Haifeng,Yan, Linjie,Wu, Yan,Lu, Yipei,Chen, Fener
, p. 5452 - 5455 (2015/11/18)
A novel asymmetric synthesis has been developed for the construction of the A-ring of a chiral precursor to calcifediol. The highlights of this synthesis include (i) the introduction of the stereochemistry at the C5-position of the A-ring through the orga
Furan approach to vitamin D analogues. Synthesis of the A-ring of calcitriol and 1α-hydroxy-3-deoxyvitamin D3
Miles, William H.,Connell, Katelyn B.,Ulas, Goezde,Tuson, Hannah H.,Dethoff, Elizabeth A.,Mehta, Varun,Thrall, April J.
supporting information; experimental part, p. 6820 - 6829 (2010/12/18)
The A-rings of calcitriol (1α,25-dihydroxyvitamin D3) and 1α-hydroxy-3-deoxyvitamin D3 were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)propanal, a diastereoselective Friedel-Crafts hydroxyalkylation, an oxidation of the 2,3-disubstituted furan to give a γ-hydroxybutenolide, and a Peterson olefination. The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield.
NOVEL METHOD OF TREATMENT OF MALE SUB-FERTILITY
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