A concise and efficient route to 2α-(ω-hydroxyalkoxy)-1α,25-dihydroxyvitamin D3: Remarkably high affinity to vitamin D receptor

Atsushi Kittaka, Yoshitomo Suhara, Hitoshi Takayanagi, Toshie Fujishima, Masaaki Kurihara, Hiroaki Takayama

Research output: Contribution to journalArticle

80 Citations (Scopus)

Abstract

(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.

Original languageEnglish
Pages (from-to)2619-2622
Number of pages4
JournalOrganic Letters
Volume2
Issue number17
Publication statusPublished - 2000 Aug 24

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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