Synthesis of novel analogues of 1alpha,25-dihydroxyvitamin D(3) with side chains at C-18.
Novel analogues of the hormone 1alpha,25-(OH)(2)-D(3) with side chains attached to C-18 were synthesized by a versatile route in which key steps were the remote radical-induced functionalization of the 18-methyl by the C-8beta-hydroxyl group and the introduction of the side chains by Wittig reactions on a C-18-aldehyde. The triene system of the novel analogues was constructed by the convergent Lythgoe-Hoffmann la Roche approach, which involves reaction of a phosphine oxide (the ring A fragment) with a ketone (the upper fragment).
Momán
Edelmiro
E
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
Nicoletti
Daniel
D
Mouriño
Antonio
A
D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013256:Steroids / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D007659:Ketones; D013256:Steroids; D002117:Calcitriol