Pyridone Annulation via Tandem Curtius Rearrangement/6π-Electrocyclization: Total Synthesis of (-)-Lyconadin C
Pyridone Annulation via Tandem Curtius Rearrangement/6π-Electrocyclization: Total Synthesis of (-)-Lyconadin C
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DOI：
10.1021/ol401954f
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发表时间：
2013-08-16
期刊：
影响因子：
5.2
通讯作者：
Waters, Stephen P.
中科院分区：
文献类型：
--
作者：
Cheng, Xiayun;Waters, Stephen P.
本文报道了石松属生物碱（-）-石松苷C的一种简便、对映选择性的全合成方法，共12步，总收率高。主要特征包括通过Mannich型环化和一锅串联Curtius重排/6 π-电环化来构建luciduline同系物，以形成lyconadin C的2-吡啶酮系统。
A concise, enantioselective total synthesis of the Lycopodium alkaloid (-)-lyconadin C was achieved in 12 steps and high overall yield. Key features include construction of a luciduline congener through Mannich-type cyclization and a one-pot, tandem Curtius rearrangement/6 pi-electrocyclization to fashion the 2-pyridone system of lyconadin C.