title: Total synthesis and antifungal activity of 9-methoxystrobilurin L as the originally proposed 1,4-benzodioxan structure.
abstract: Total synthesis of both enantiomers of 9-methoxystrobilurin L as the originally proposed 1,4-benzodioxan structure was successfully achieved. The 1H and 13C NMR spectra of synthesized 9-methoxystrobilurin L were compared with those of a naturally-occurring sample. It was strongly indicated that naturally-occurring 9-methoxystrobilurin L has not the originally reported 1,4-benzodioxan structure but a 1,5-benzodioxepin structure, the same as previously reported 9-methoxystrobilurin K. Antifungal activities of the synthesized compounds toward several typical fungi were also examined, and they were less active than 9-methoxystrobilurin K.
authors.affiliation: Faculty of Pharmaceutical Sciences, Science University of Tokyo, Ichigaya-Funagawara-machi, Shinjuku-ku, 162-0826, Tokyo, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Aiba
authors.forename: D
authors.initials: D
authors.lastname: Hasegawa
authors.forename: T
authors.initials: T
authors.lastname: Marunouchi
authors.forename: K
authors.initials: K
authors.lastname: Nagasawa
authors.forename: H
authors.initials: H
authors.lastname: Uchiro
authors.forename: S
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000187:drug effects; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010407:Penicillium / Q000187:drug effects
chemical_list: C440497:9-methoxystrobilurin K; C101802:9-methoxystrobilurin L; D000179:Acrylates; D000935:Antifungal Agents; D004148:Dioxolanes; D004852:Epoxy Compounds