Short Synthesis of the Tricyclic Core Common to Lycopodine-Like Lycopodium Alkaloids: Discovery of a Separable Pair of Keto-Enol Tautomers
Published Web Location
https://doi.org/10.1021/acs.orglett.5c02091
Abstract
The effective synthesis of strained Lycopodium alkaloids bearing lycopodine-like frameworks, categorized as miscellaneous, continues to pose significant synthetic challenges. Herein, we outline a concise and scalable strategy for the construction of the ABC tricyclic core of this class of natural products that is amenable to asymmetric synthesis. A tandem Michael-Claisen condensation enables rapid assembly of the core structure while offering prospects for derivatization. In the process, a pair of keto-enol tautomers that could be separated and characterized at room temperature was discovered.
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