Total Synthesis of Gelsedilam by Means of a Thiol‐Mediated Diastereoselective Conjugate Addition–Aldol Reaction |
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| Authors: | Dr. You‐Ming Huang Dr. Yang Liu Dr. Chang‐Wu Zheng Qiao‐Wen Jin Lu Pan Ren‐Ming Pan Jun Liu Prof. Dr. Gang Zhao |
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| Affiliation: | Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China |
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| Abstract: | The total synthesis of gelsedilam, which features a highly diastereoselective thiol conjugate addition–intramolecular aldol reaction to install the strained and caged [3.2.2] bridged ring system and highly efficient NiCl2/NaBH4‐mediated four‐step transformation in one‐pot to construct its five‐membered lactam ring is reported. The synthesis requires only 18 linear steps from the known compounds, providing useful strategies for the construction of the intricate ring system in the synthesis of related gelsedine‐type alkaloids. |
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| Keywords: | aldol reaction alkaloids gelsedilam gelsedine total synthesis |
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