（-）-FR901483 和（+）-8-epi-FR901483 的对映选择性全合成。

Enantioselective total syntheses of (-)-FR901483 and (+)-8-epi-FR901483.

机构信息

Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.

出版信息

J Org Chem. 2013 Jan 18;78(2):455-65. doi: 10.1021/jo302362b. Epub 2012 Dec 18.

DOI:10.1021/jo302362b

PMID:23214918

Abstract

The enantioselective total syntheses of the potent immunosuppressant FR901483 (1) and its 8-epimer (47) have been accomplished. Our approach features the use of building block 6 as the chiron, the application of the one-pot amide reductive bis-alkylation method to construct the chiral aza-quaternary center (dr = 9:1), regio- and diastereoselective intramolecular aldol reaction to build the bridged ring, and RCM to form the 3-pyrrolin-2-one ring.

摘要

我们已经完成了强效免疫抑制剂 FR901483（1）及其 8-差向异构体（47）的对映选择性全合成。我们的方法以砌块 6 作为手性中心，采用一锅酰胺还原双烷基化方法构建手性氮杂季碳中心（dr = 9:1），区域和立体选择性的分子内 aldol 反应构建桥环，以及 RCM 形成 3-吡咯啉-2-酮环。