title: Synthesis of the 3-methylene-2-vinyltetrahydropyran unit; the hallmark of the sesquiterpene, hodgsonox.
abstract: [structure: see text] The synthesis of some simple compounds containing the previously unreported 3-methylene-2-vinyltetrahydropyran system, a unique feature of the liverwort metabolite, hodgsonox is reported. Key features are the creation of an acrolein substituted in the alpha-position with a three-carbon chain bearing a terminal electrophilic site, addition of a vinyl group, and cyclization.
authors.affiliation: Department of Chemistry, University of Otago, Box 56, Dunedin, New Zealand.
authors.forename: Anna J
authors.initials: AJ
authors.lastname: Barlow
authors.forename: Benjamin J
authors.initials: BJ
authors.lastname: Compton
authors.forename: Rex T
authors.initials: RT
authors.lastname: Weavers
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D011714:Pyrans; D014753:Vinyl Compounds; C500468:hodgsonox