Ruth P. Paulino , Karen Ichikawa , Jonathan Sperry
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引用次数: 0
摘要
阴毛酰胺 A 和 B 是一种结构不寻常的单萜烯 N-苯甲酰基酰胺，它们是从一种具有已知精神药物特性的热带果树 Casimiroa pubescens 中分离出来的。在此，我们报告了通过化学合成确认这两种天然产物结构的方法，该方法的特点是在 Hoveyda-Grubbs 第二代催化剂存在下，1,1-二取代烯和二烯酮之间发生路易斯酸辅助的交叉甲基化反应。立体化学纯度较高的短叶酰胺 A 和 B 样品在静置后会发生异构化，这表明它们都是真正的天然产物。
Synthesis and structural affirmation of pubesamides A and B, monoterpene N-benzoyltyramides from white sapote (Casimiroa pubescens)
Pubesamides A and B are structurally unusual monoterpene N-benzoyltyramides isolated from Casimiroa pubescens, a tropical fruiting tree with known psychotropic properties. Herein we report the structural affirmation of both natural products through a chemical synthesis that features a Lewis-acid assisted cross-metathesis reaction between a 1,1-disubstituted alkene and a dienone in the presence of the Hoveyda-Grubbs second generation catalyst. Stereochemically pure samples of pubesamide A and B isomerise upon standing, suggesting they are both genuine natural products.
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