Total Synthesis of a Pancratistatin/Shikimic Acid Hybrid Analogue

Abstract

Pancratistatin and structurally related narciclasine are natural products of great interest as they display potent and selective activities against various diseases. A concise synthesis of a functionalised pancratistatin framework, via a Heck reaction and subsequent cyclisation, is reported. The unfunctionalised model core of pancratistatin was synthesised from 1‐cyclohexene‐1‐carboxylic acid in two‐steps in 50% yield. A modified route was then successfully applied to (−)‐shikimic acid to afford a novel pancratistatin/shikimic acid hybrid analogue that possesses three stereo‐defined hydroxyl groups in the C‐ring.