University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, United Kingdom.
Org Lett. 2010 Feb 19;12(4):680-3. doi: 10.1021/ol902638w.
A general steroid synthesis is presented that relies on prior formation of three stereogenic centers (C8, C13, and C14) on a D ring template, followed by C- and B-ring cyclizations. The assembly of the key D ring template, achieved by a 3-component conjugate addition/alkylation process, allows introduction of structural variety as required. The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization.
本文提出了一种通用的甾体合成方法，该方法依赖于在 D 环模板上预先形成三个立体中心（C8、C13 和 C14），然后进行 C-和 B-环环化。关键的 D 环模板的组装通过三组分共轭加成/烷基化过程实现，允许根据需要引入结构多样性。该方法通过 C-环闭环复分解和 B-环 Heck 环化反应，以雌酮的全合成为例进行了说明。
