Total Synthesis of a Pancratistatin/Shikimic Acid Hybrid Analogue

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. A concise synthesis of the 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. image