Δ22-Unsaturated analogs of vitamin D3 and their C(1)-hydroxylated derivatives

摘要: Abstract A stereospecific synthesis of (22 E )- and Z )-dehydrocholecalciferols is described starting from C-22 steroidal aldehydes. Direct C(1) hydroxylation these compounds was achieved via oxidation the 3,5-cyclovitamin D intermediates with SeO 2 t -butylhydroperoxide , affording 1α-hydroxyvitamin 3 Δ 22 -unsaturated side chain. In addition, their 5,6- trans isomers 1β epimers have been prepared. The ) isomer as active vitamin or in its ability to mibilize bone calcium heal rickets rats, whereas compound less effective. Bioassay corresponding 1α-hydroxylated analogs showed - -1 α -hydroxyvitamin be equal mobilizing healing rickets, cis active. C(1)-hydroxylated vitamins were tested for bind chick intestinal receptor protein 1,25-dihydroxyvitamin . Both found somewhat more potent than displacement tritiated