Momán Edelmiro, Nicoletti Daniel, Mouriño Antonio
Departamento de Química Orgánica y Unidad Asociada al CSIC, Universidad de Santiago de Compostela, E-15782 Santiago de Compostela, Spain.
J Org Chem. 2004 Jul 9;69(14):4615-25. doi: 10.1021/jo0498664.
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).
通过一种通用方法合成了激素1α,25-(OH)₂-D₃的新型类似物，其侧链连接在C-18位，关键步骤包括C-8β-羟基对18-甲基的远程自由基诱导官能化以及通过C-18醛上的维蒂希反应引入侧链。新型类似物的三烯系统通过收敛性的利斯戈-霍夫曼·罗氏方法构建，该方法涉及氧化膦（A环片段）与酮（上片段）的反应。
