Stereoselective Total Synthesis of (±)-Alstoscholarisine E.
Stereoselective Total Synthesis of (±)-Alstoscholarisine E.
复制标题
(±)-Alstoscholarisine E 的立体选择性全合成。
DOI：
10.1021/acs.orglett.9b04093
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发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
Martin,StephenF
中科院分区：
文献类型：
--
作者：
Wood,MichaelD;Klosowski,DanielW;Martin,StephenF
迄今为止合成（±）-alstoscholarisine E最短的方法是用市售试剂在7个线性步骤中完成的，总收率为15.2%。该方法的特点是串联vinyous Mannich反应和hetero-Diels-Alder反应，以进入核心。发现了一种诱导环乙烯醚非对映选择性还原的新策略，并开发了一种通过铱催化硅氢化反应部分还原内酰胺环形成桥化动物环的温和方法。
The shortest synthesis to date of (±)-alstoscholarisine E was accomplished in seven linear steps from commercially available reagents and 15.2% overall yield. The approach features a tandem vinylogous Mannich reaction and hetero-Diels–Alder reaction to access the core. A novel tactic to induce diastereoselective reduction of the cyclic vinyl ether was discovered, and a mild procedure to form the bridged aminal ring by partial reduction of the lactam ring via iridium-catalyzed hydrosilylation was developed.