Departamento de Química Orgánica (Módulo 01), Universidad Autónoma de Madrid, c/Francisco Tomas y Valiente 7, Cantoblanco, 28049-Madrid, Spain.
Org Lett. 2010 Feb 5;12(3):580-3. doi: 10.1021/ol9027804.
The asymmetric synthesis of the natural gamma-tocopherol metabolite (S)-gamma-CEHC (1) is described in 10 steps and 18.4% overall yield starting from 2,3-dimethylhydroquinone. The key step is a stereoselective TiCl(4)-mediated homochiral sulfoxide-directed allylation of ketal (SS)-3 to efficiently generate the challenging C-2 stereogenic carbon of chroman (SS,S)-2 with the correct absolute configuration.
本文描述了从 2,3-二甲基对苯二酚出发，经 10 步反应以 18.4%的总收率不对称合成天然 γ-生育酚代谢物 (S)-γ-CEHC（1）。关键步骤是立体选择性 TiCl4 介导的手性亚砜导向的酮缩醇（SS）-3 的烯丙基化反应，高效地生成具有正确绝对构型的色满（SS，S）-2 的挑战性 C-2 立体手性碳。
