title: Total synthesis of (-)-ophiodilactone A and (-)-ophiodilactone B.
abstract: The first asymmetric total synthesis of (-)-ophiodilactone A and (-)-ophiodilactone B, isolated from the ophiuroid (Ophiocoma scolopendrina), is reported. The key features of the synthesis include the highly stereocontrolled construction of the structurally congested γ-lactone/δ-lactone skeleton through an asymmetric epoxidation, diastereoselective iodolactonization, and intramolecular epoxide-opening with a carboxylic acid, and biomimetic radical cyclization of ophiodilactone A to ophiodilactone B.
authors: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521 (Japan).
authors: Takaaki
authors: T
authors: Matsubara
authors: Keisuke
authors: K
authors: Takahashi
authors: Jun
authors: J
authors: Ishihara
authors: Susumi
authors: S
authors: Hatakeyama
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001555:Benzene Derivatives; D004852:Epoxy Compounds; D005609:Free Radicals; D007783:Lactones; C542751:ophiodilactone A; C542752:ophiodilactone B
keywords: asymmetric synthesis; bioinspired synthesis; radical coupling; total synthesis