title: Total synthesis of nominal lyngbouilloside aglycon.
abstract: The first enantioselective total synthesis of the originally assigned structure of lyngbouilloside aglycon has been achieved using a particularly flexible route featuring an acylketene macrolactonization of a tertiary methyl carbinol as the key step. Comparison of the C13 chemical shifts of our synthetic aglycon with the ones pertaining to natural lyngbouilloside and lyngbyaloside C resulted in a possible stereochemical reassignment of the C11 stereogenic center.
authors.affiliation: Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 rue Vauquelin, 75231 Paris Cedex 05, France.
authors.forename: Abdelatif
authors.initials: A
authors.lastname: ElMarrouni
authors.forename: Raphael
authors.initials: R
authors.lastname: Lebeuf
authors.forename: Julian
authors.initials: J
authors.lastname: Gebauer
authors.forename: Montserrat
authors.initials: M
authors.lastname: Heras
authors.forename: Stellios
authors.initials: S
authors.lastname: Arseniyadis
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
mesh_terms: D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D018942:Macrolides; C464989:lyngbouilloside; C571265:lyngbouilloside aglycon