Synthesis of novel analogues of 1alpha,25-dihydroxyvitamin D(3) with side chains at C-18 |
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Authors: | Momán Edelmiro Nicoletti Daniel Mouriño Antonio |
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Institution: | Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain. |
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Abstract: | 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). |
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