Synthesis and structural affirmation of pubesamides A and B, monoterpene N-benzoyltyramides from white sapote (Casimiroa pubescens)

Synthesis and structural affirmation of pubesamides A and B, monoterpene N-benzoyltyramides from white sapote (Casimiroa pubescens)

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Pubesamides A and B are structurally unusual monoterpene N-benzoyltyramides isolated from Casimiroa pubescens, a tropical arcade smokey the bear belt 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 here second generation catalyst.Stereochemically pure samples of pubesamide A and B isomerise upon standing, suggesting they are both genuine natural products.