Practical isolation of polygodial from Tasmannia lanceolata: a viable scaffold for synthesis

Polygodial, a valuable sesquiterpene dialdehyde featuring an epimerizable stereocenter was efficiently extracted and isolated in gram-scale quantities (3.3% w/w) from <em>Tasmannia lanceolata</em> (Tasmanian native pepper) <em>via</em> a recently developed rapid pressurised hot water extraction (PHWE) technique that utilises an unmodified household espresso machine. This method was compared to the maceration of <em>T. lanceolata</em> under a range of conditions. Polygodial was used to achieve semi-syntheses of closely related sesquiterpene natural products drimendiol, (−)-drimenol, (+)-euryfuran, and some non-natural derivatives.