Synthesis of the 3-methylene-2-vinyltetrahydropyran unit; the hallmark of the sesquiterpene, hodgsonox.
[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.
Barlow
Anna J
AJ
Department of Chemistry, University of Otago, Box 56, Dunedin, New Zealand.
Compton
Benjamin J
BJ
Weavers
Rex T
RT
D009682:Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D014753:Vinyl Compounds / Q000737:chemistry*
D011714:Pyrans; D014753:Vinyl Compounds; C500468:hodgsonox