オキセタン構造を有するビタミンD_3誘導体の合成

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タイトル別名
  • Synthesis of novel vitamin D_3 analogues having a spiro-oxetane structure
  • オキセタン コウゾウ オ ユウスル ビタミン D ₃ ユウドウタイ ノ ゴウセイ

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抄録

Two novel stereoisomeric analogues of active vitamin D, 1,25-dihydroxyvitamin D_3, in which a spirooxetane structure exists at the C3 position of the A-ring, have been designed and synthesized in a convergent manner. This is the first attempt to utilize spiro-oxetane structures as surrogates of vital hydroxy groups in vitamin D analogues. The enyne precursors, which were required for the construction of the A-ring, were prepared from 3,3-bis(2-hydroxyethyl)oxetane in excellent yield according to the eight-step procedure. The absolute configuration at the C1-position of the synthesized compounds was determined by the circular dichroism exciton chirality method using the corresponding C1-allylic benzoates. The replacement of the C3-hydroxy group of active vitamin D with a spiro-oxetane structure provided more preferable conformation for its binding to vitamin D receptors by shifting the conformational equilibrium of the A-ring to its β-chair form.

収録刊行物

  • ビタミン

    ビタミン 90 (3), 109-114, 2016

    公益社団法人 日本ビタミン学会

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