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

Organic & Biomolecular Chemistry Pub Date: 2015-09-10 DOI: 10.1039/C5OB01573A

Abstract

Polygodial, a valuable sesquiterpene dialdehyde featuring an epimerizable stereocenter was efficiently extracted and isolated in gram-scale quantities (3.3% w/w) from Tasmannia lanceolata (Tasmanian native pepper) via 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 T. lanceolata 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.

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