Dr. Reddy's Institute of Life Sciences (DRILS) , University of Hyderabad Campus, Hyderabad 500046, India.
Org Lett. 2015 Feb 6;17(3):468-71. doi: 10.1021/ol503464s. Epub 2015 Jan 12.
A practical stereoselective synthesis to obtain the substituted furan ring as the substructure of eribulin is developed. An asymmetric syn-aldol and intramolecular oxy-Michael were two key steps in our approach. The functionalized furan derivatives were then utilized further to build the 14- and 12-membered macrocyclic diversity as trans- and cis-fused (C-29 and C-30) compounds. This is the first report of building a chemical toolbox with macrocyclic small molecules having trans- or cis-fused 14- or 12-membered rings containing the substructure of eribulin and its diastereomer.
开发了一种实用的立体选择性合成方法，以获得作为埃博霉素亚结构的取代呋喃环。我们的方法中包含两个关键步骤：不对称 syn-aldol 和分子内氧迈克尔加成。然后，进一步利用功能化的呋喃衍生物构建 14 元和 12 元大环多样性，作为反式和顺式（C-29 和 C-30）化合物。这是第一个报告使用大环小分子构建化学工具箱的例子，这些小分子包含埃博霉素及其非对映异构体的反式或顺式 14 元或 12 元环亚结构。
