Metabolic pathway leading to the biologically active form of vitamin D � 1a,25-dihydroxyvitamin D3 (calcitriol) consists of two subsequent enzymatic hydroxylations of vitamin D3. This, in turn, is produced in the skin from previtamin D3 derived from 7-dehydrocholesterol. An antarafacial [1,7]-hydrogen shift is observed in the conversion of previtamin D form to vitamin D triene system. In the case of vitamin D3, hydrogen is reversibly migrating from methyl group at C-10 to sp2 carbon (C-19) with simultaneous rearrangement of the double bonds system. Here we describe the synthesis and thermal isomerization of 9-substituted analogues of 1a,25-dihydroxyprevitamin D3. The synthesized compounds can be potentially useful in treatment of diseases related to bone mineralization or abnormal cell cycle.

Sigmatropic rearrangement leading to new vitamin D<sub>3</sub> analogs with unnatural triene system

244th National Meeting (2012)

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Sigmatropic rearrangement leading to new vitamin D3 analogs with unnatural triene system

Sigmatropic rearrangement leading to new vitamin D₃ analogs with unnatural triene system