Diversity-Oriented Synthesis of Diverse Polycyclic Scaffolds Inspired by the Logic of Sesquiterpene Lactones Biosynthesis

Gaelle Valot, Jose Garcia, Vincent Duplan, Christelle Serba, Sofia Barluenga and
Nicolas Winssinger Angew. Chem. Int. Ed.

Farnesyl diphosphate is the substrate for the biosynthesis of over five thousand sesquiterpene lactone natural products with a wide array of molecular scaffolds.

Inspired by the natural diversity achieved by sesquiterpene synthases, Winssinger and co-workers demonstrate diverse scaffold synthesis from a similar (though differentially functionalised and stereochemically well defined) acyclic substrate employing various transition metal-catalysed conditions.

Using gold, platinum or Grubbs catalysts, and either a protected or free hydroxyl group, a diverse series of scaffolds were made. The authors point out that 2 of these scaffolds are unprecedented while the others are common structures in sesquiterpene lactones. Unfortunately, palladium and rhodium catalysts failed to give any cyclisation products. The authors go on to show how simple modifications of one scaffold can lead to natural sesquiterpene lactone structures.

DOI: 10.1002/anie.201201157


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