Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions

…, CW Boyce, MA Labroli, CA Sehon, Q Jin

文献索引：Boger, Dale L.; Boyce, Christopher W.; Labroli, Marc A.; Sehon, Clark A.; Jin, Qing Journal of the American Chemical Society, 1999 , vol. 121, # 1 p. 54 - 62

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被引用次数: 391

摘要

Concise, efficient total syntheses of ningalin A (1), lamellarin O (2), lukianol A (3), and permethyl storniamide A (5) are detailed on the basis of a common heterocyclic azadiene Diels-Alder strategy (1, 2, 4, 5-tetrazine→ 1, 2-diazine→ pyrrole) ideally suited for construction of the densely functionalized pyrrole cores found in the three classes of marine natural products. Examination of the natural products and a number of synthetic ...