Organocatalytic, Asymmetric Synthesis of Aza-Quaternary Center of Izidine Alkaloids: Synthesis of (−)-Tricyclic Skeleton of Cylindricine

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• 作者：Kyatham Srinivas ; Nishant Singh ; Dinabandhu Das ; Dipankar Koley
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：19
• 期：1
• 页码：274-277
• 全文大小：462K
• ISSN：1523-7052

文摘

We report a highly efficient, enantioselective, organocatalytic method for the synthesis of izidinone alkaloids containing a bridgehead aza-quaternary center using ketone-derived N,O-hemiaminal with a tethered acetal. Alkyl-, aryl-, and alkenyl-substituted substrates cyclize to the respective products with excellent enantioselectivities. Five- and seven-membered ring formation has also been established. Furthermore, synthesis of the tricyclic skeleton of cylindricine alkaloids has been achieved in high yield.