以乌吉四组分偶联反应和显著选择性消除反应为特色的FR901483三环核心结构的合成
A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.
作者信息
Seike Hirofumi, Sorensen Erik J
机构信息
Frick Chemical Laboratory, Princeton University, Princeton, NJ 08544-1009, USA, Fax +1(609)2581980.
出版信息
Synlett. 2008 Mar 18;2008(5):695-701. doi: 10.1055/s-2008-1042813.
Abstract
Three key reactions, an efficient Ugi four-component coupling, a regiospecific, base-mediated elimination reaction, and an intramolecular nitrone/alkene [3+2] cycloaddition, were used to achieve an effective synthesis of the tricyclic molecular framework of the immunosuppressant FR901483. The outcome of a control experiment supports the idea that an internal deprotonation by an alkoxide ion is the origin of the site selectivity observed in the base-induced elimination of hydroxy mesylate 17.
摘要
通过三个关键反应，即高效的乌吉四组分偶联反应、区域特异性的碱介导消除反应以及分子内硝酮/烯烃的[3+2]环加成反应，实现了免疫抑制剂FR901483三环分子骨架的有效合成。对照实验的结果支持了这样一种观点，即醇盐离子的内部去质子化是在碱诱导的羟基甲磺酸酯17消除反应中观察到的位点选择性的起源。
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