TY - JOUR
T1 - A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3
T2 - Remarkably high affinity to vitamin D receptor
AU - Kittaka, Atsushi
AU - Suhara, Yoshitomo
AU - Takayanagi, Hitoshi
AU - Fujishima, Toshie
AU - Kurihara, Masaaki
AU - Takayama, Hiroaki
PY - 2000/8/24
Y1 - 2000/8/24
N2 - (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.
AB - (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.
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U2 - 10.1021/ol006222j
DO - 10.1021/ol006222j
M3 - Article
C2 - 10990411
AN - SCOPUS:0034710456
SN - 1523-7060
VL - 2
SP - 2619
EP - 2622
JO - Organic Letters
JF - Organic Letters
IS - 17
ER -