title: Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction.
abstract: A general and efficient synthesis of the 2H-tetrahydro-4,6-dioxo-1,2-oxazine ring system through a tandem nucleophilic addition and transesterification reaction is described. The reaction is highly functional-group-tolerant and proceeds under mild conditions, affording the corresponding products in good to excellent yields. This method represents the first general synthetic route to access this heterocyclic scaffold, which exists in the complex natural products alchivemycin A and B with significant antibiotic activities.
authors: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, China.
authors: Shaoqiang
authors: S
authors: Yang
authors: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, China.
authors: Daohong
authors: D
authors: Liao
authors: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, China.
authors: Xiaoqi
authors: X
authors: Tian
authors: School of Pharmaceutical Science and Technology, Tianjin University , Tianjin 300072, China.|Beijing National Laboratory of Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Department of Chemical Biology, College of Chemistry and Molecular Engineering, Synthetic and Functional Biolmolecules Center, and Center for Life Sciences, Peking University , Beijing 100871, China.
authors: Xiaoguang
authors: X
authors: Lei
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology; D018942:Macrolides / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: C000608192:2H-tetrahydro-4,6-dioxo-1,2-oxazine; D000900:Anti-Bacterial Agents; D001688:Biological Products; D018942:Macrolides; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; D010078:Oxazines; C553074:alchivemycin A; C585985:alchivemycin B; C015388:nitrones; D015032:Zinc