Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation

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• 作者：Liao-Bin Dong ; Ya-Nan Wu ; Shi-Zhi Jiang ; Xing-De Wu ; Juan He ; Yu-Rong Yang ; Qin-Shi Zhao
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 16, 2014
• 年：2014
• 卷：16
• 期：10
• 页码：2700-2703
• 全文大小：293K
• 年卷期：v.16,no.10(May 16, 2014)
• ISSN：1523-7052

文摘

Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C₁₇N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymmetric total synthesis. Following the first total synthesis of lobscurinine (3), 1 was achieved via regio- and stereoselective cyanide ion addition and subsequent acid treatment.