A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.
A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.
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DOI：
10.1021/acs.orglett.6b01674
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发表时间：
2016-08-19
期刊：
影响因子：
5.2
通讯作者：
Brewer M
中科院分区：
文献类型：
--
作者：
Giampa GM;Fang J;Brewer M
报道了一个短的合成序列，导致形成Aspidosperma生物碱的C，D，E环亚基。该路线是基于环断裂/分子内甲亚胺叶立德1，3-偶极环加成反应序列，得到作为单一非对映异构体的所需三环产物。在刘易斯酸存在下，γ-氨基-β-羟基-α-重氮羰基化合物发生断裂，生成亚胺盐，亚胺盐可直接还原为相应的胺。
A short synthetic sequence leading to the formation of the C,D,E-ring subunit of the Aspidosperma alkaloids is reported. This route is based on a ring fragmentation/intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction sequence that gives the desired tricyclic product as a single diastereomer. A γ-amino-β-hydroxy-α-diazo carbonyl compound is shown to fragment in the presence of a Lewis acid to give an iminium product that can be directly reduced to the corresponding amine.