Total synthesis of Punicagranine

Tetrahedron Letters
2019.0

Abstract

This communication details the first total synthesis of Punicagranine, a new pyrrolizine alkaloid isolated from the peels of the pomengranate, Punica granatum, the basis for traditional Chinese medicine, with anti-inflammatory activity. Two concise, 4–5 step routes were developed to rapidly prepare Punicagranine in 10.7–12.1% overall yields. One route features an intramolecular Heck reaction, while the other relies on a 1,3-dipolar cycloaddition. The latter route proceeds on scale to support future biological studies. © 2019 Elsevier Ltd

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