title: Stereoselective synthesis of the published structure of feigrisolide A. Structural revision of feigrisolides A and B.
abstract: The total synthesis of the proposed structure of feigrisolide A is reported. Ethyl (S)-3-hydroxybutyrate was the chiral starting material. A Brown asymmetric allylation and an Evans aldol reaction were key steps of the synthesis. The NMR data of the synthetic product are different from those of the natural product. The published structure of feigrisolide A is therefore erroneous. A subsequent comparison of spectral data strongly suggests that feigrisolides A and B are identical with (-)-nonactic acid and (+)-homononactic acid, respectively.
authors.affiliation: Departamento de Química Inorganica y Organica, Universidad Jaume I, E-12071 Castellón, Spain.
authors.forename: Paula
authors.initials: P
authors.lastname: Alvarez-Bercedo
authors.forename: Juan
authors.initials: J
authors.lastname: Murga
authors.forename: Miguel
authors.initials: M
authors.lastname: Carda
authors.forename: J Alberto
authors.initials: JA
authors.lastname: Marco
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D007783:Lactones; C417114:feigrisolide A; C417115:feigrisolide B