96685-53-9Relevant articles and documents
Total synthesis of biologically active 20S-hydroxyvitamin D3
Wang, Qinghui,Lin, Zongtao,Kim, Tae-Kang,Slominski, Andrzej T.,Miller, Duane D.,Li, Wei
, p. 153 - 162 (2015/12/01)
A total synthetic strategy of 20S-hydroxyVitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig-Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated Vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.
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
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, (2008/06/13)
There is provided a method of prevention of adhesions, eg surgical adhesions, which comprises using a vitamin D compound.