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.