从常见中间体不对称合成天然和非天然二苄基丁烷木脂素。

Asymmetric Synthesis of Natural and Unnatural Dibenzylbutane Lignans from a Common Intermediate.

机构信息

Departments of Pharmacology and Chemistry, Vanderbilt Center for Neuroscience Drug Discovery , Vanderbilt University , Nashville , Tennessee 37232 , United States.

出版信息

J Org Chem. 2019 May 3;84(9):5974-5979. doi: 10.1021/acs.joc.9b00633. Epub 2019 Apr 24.

DOI:10.1021/acs.joc.9b00633

PMID:31002498

Abstract

Lignans are a structurally diverse class of natural products with extensive pharmacological effects. Here we report the syntheses of both natural and unnatural dibenzylbutane lignans from a common intermediate, which is prepared in five steps from known materials. Derivatization of this intermediate affords lignans featuring contiguous stereocenters in a high diastereomeric purity after chromatography. This divergent synthetic route can be exploited to prepare dibenzylbutane lignans and analogues thereof to probe their biological profiles.

摘要

木脂素是一类具有广泛药理作用的结构多样的天然产物。在这里，我们报告了从一种常见的中间体合成天然和非天然二苄基丁烷木脂素，该中间体可从已知材料经五步反应制得。该中间体的衍生化在经过色谱分离后可得到具有连续立体中心的木脂素，其具有很高的非对映体纯度。这种发散的合成途径可用于制备二苄基丁烷木脂素及其类似物，以研究它们的生物学特性。