title: Practical isolation of polygodial from Tasmannia lanceolata: a viable scaffold for synthesis.
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.
authors.affiliation: School of Physical Sciences - Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia. Jason.Smith@utas.edu.au Alex.Bissember@utas.edu.au.
authors.forename: Jeremy
authors.initials: J
authors.lastname: Just
authors.affiliation: School of Physical Sciences - Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia. Jason.Smith@utas.edu.au Alex.Bissember@utas.edu.au and Analytical Sciences Tasmania, New Town, Tasmania, 7008, Australia.
authors.forename: Timothy B
authors.initials: TB
authors.lastname: Jordan
authors.affiliation: School of Physical Sciences - Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia. Jason.Smith@utas.edu.au Alex.Bissember@utas.edu.au and Australian Centre for Research on Separation Science (ACROSS), University of Tasmania, Hobart, Tasmania, 7001, Australia.
authors.forename: Brett
authors.initials: B
authors.lastname: Paull
authors.affiliation: School of Physical Sciences - Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia. Jason.Smith@utas.edu.au Alex.Bissember@utas.edu.au.
authors.forename: Alex C
authors.initials: AC
authors.lastname: Bissember
authors.affiliation: School of Physical Sciences - Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia. Jason.Smith@utas.edu.au Alex.Bissember@utas.edu.au.
authors.forename: Jason A
authors.initials: JA
authors.lastname: Smith
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry; D032423:Winteraceae / Q000737:chemistry*
chemical_list: D001688:Biological Products; D005663:Furans; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D013729:Terpenes; C481244:drimenol; C034380:polygodial; C039281:furan