Abstract
Replacing carbon-hydrogen bonds with carbon-fluorine bonds has been studied for a long time for the improvement of pharmacological activity from the viewpoint of 1) enhancing interaction with the target biological components based on molecular polarity changes and conformational changes on the molecule derived from the large electronegativity of fluorine, 2) obtaining stability against catabolism based on the large carbon-fluorine bond energy, and 3) improving the lipophilicity of the molecule into which fluorine was introduced (on the contrary, fat solubility decreases in some cases). In the vitamin D research field, fluorination has been progressing from the 1st position to the 27th position in the vitamin D3 molecule. This mini review outlines the fluorinated vitamin D synthesis reported so far and introduces our improved synthetic methods of fluorination on the vitamin D side chain and also new fluorinated vitamin D derivatives.
