title: Total Synthesis of Plakilactones C, B and des-Hydroxyplakilactone B by the Oxidative Cleavage of Gracilioether Furanylidenes.
abstract: A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl4.
authors.affiliation: School of Chemical and Physical Sciences, Flinders University , GPO Box 2100, Adelaide, SA 5001, Australia.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Norris
authors.affiliation: School of Chemical and Physical Sciences, Flinders University , GPO Box 2100, Adelaide, SA 5001, Australia.
authors.forename: Michael V
authors.initials: MV
authors.lastname: Perkins