title: A Formal Approach to Xylosmin and Flacourtosides E and F: Chemoenzymatic Total Synthesis of the Hydroxylated Cyclohexenone Carboxylic Acid Moiety of Xylosmin.
abstract: The hydroxylated cyclohexenone carboxylic acid moiety of xylosmin was synthesized in eight steps from benzoic acid. The key steps in the synthesis involved the enzymatic dihydroxylation of benzoic acid by the whole cell fermentation with Ralstonia eutrophus B9, and Henbest epoxidation. Early attempts led to the synthesis of a C6 epimer of the methyl ester of the hydroxylated cyclohexenone carboxylic acid moiety. The absolute stereochemistry of an advanced intermediate was confirmed by X-ray crystallography. Complete characterization of the previously reported but not fully characterized hydroxylated cyclohexenone carboxylic acid is provided.
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University , St. Catharines, ON L2S 3A1, Canada.
authors.forename: Mukund
authors.initials: M
authors.lastname: Ghavre
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University , St. Catharines, ON L2S 3A1, Canada.
authors.forename: Jordan
authors.initials: J
authors.lastname: Froese
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University , St. Catharines, ON L2S 3A1, Canada.
authors.forename: Brennan
authors.initials: B
authors.lastname: Murphy
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University , St. Catharines, ON L2S 3A1, Canada.
authors.forename: Razvan
authors.initials: R
authors.lastname: Simionescu
authors.affiliation: Department of Chemistry and Centre for Biotechnology, Brock University , St. Catharines, ON L2S 3A1, Canada.
authors.forename: Tomas
authors.identifier: 0000-0003-3239-6815
authors.initials: T
authors.lastname: Hudlicky