Diastereoselective synthesis of glutamate-appended oxolane rings: synthesis of (s)-(+)-lycoperdic acid.
Diastereoselective synthesis of glutamate-appended oxolane rings: synthesis of (s)-(+)-lycoperdic acid.
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谷氨酸附加的四氢呋喃环的非对映选择性合成：(s)-( )-番茄酸的合成。
DOI：
10.1021/jo7017137
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发表时间：
2007
期刊：
影响因子：
--
通讯作者：
Chamberlin,ARichard
中科院分区：
文献类型：
--
作者：
Cohen,JamieL;Chamberlin,ARichard
描述了含谷氨酸天然产物(S)-(+)-番茄红素酸的立体控制合成。合成路线的关键转化是在焦谷氨酸支架上有效的非对映选择性环化oxolane环，以构建γ，γ-二取代谷氨酸-附加四氢呋喃或γ-内酯。该反应序列还改进了焦谷氨酸衍生物的高收率卤化方法，增强了立体选择。
The stereocontrolled synthesis of the glutamate-containing natural product (S)-(+)-lycoperdic acid is described. The key transformation in the synthetic route was an efficient diastereoselective annulation of an oxolane ring onto a pyroglutamate scaffold to construct either a γ,γ-disubstituted glutamate-appended tetrahydrofuran or a γ-lactone. The reaction sequence also featured an improved method for the halogenation of pyroglutamate derivatives in high yield with enhanced stereoselection.