Synthesis of new aromatic (C17-C20)-locked side-chain analogues of calcitriol (1alpha,25-dihydroxyvitamin D(3)).
The synthesis of four new analogues of calcitriol (1alpha, 25-(OH)(2)-D(3)) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.
Fernández-Gacio
A
A
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, 15706 Santiago de Compostela, Spain.
Vitale
C
C
Mouriño
A
A
D000818:Animals; D001667:Binding, Competitive; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D002417:Cattle; D066298:In Vitro Techniques; D008968:Molecular Conformation; D018167:Receptors, Calcitriol / Q000378:metabolism; D013950:Thymus Gland / Q000378:metabolism
D018167:Receptors, Calcitriol; D002117:Calcitriol