(equation presented) A convenient and potentially valuable synthetic approach to the novel 2α-functionalized 1α,25-dihydroxyvitamin D3 [1α,25(OH)2D3] derivatives (1a-c), which are the C2-epimer of ED-71 and its analogues, has been developed. The C2α-modified ring A precursors (1,7-enynes 16, n = 0, 1, and 2) were constructed stereoselectively starting from D-glucose in high yield. In the synthesized 2α-(ω-hydroxyalkoxy)-1α,25(OH)2D3 derivatives, 1a and 1b showed a greater binding affinity to vitamin D receptor (VDR), up to 1.8 times that of the native hormone.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry