title: An efficient method for the synthesis of enol ethers and enecarbamates. Total syntheses of isoindolobenzazepine alkaloids, lennoxamine and chilenine.
abstract: An efficient method for the synthesis of enol ethers and enecarbamates has been developed based on catalytic hydrosilane reduction of alpha-phosphonoxy enol ethers and alpha-phosphonoxy enecarbamates. This method has been applied to the total syntheses of two isoindolobenzazepine alkaloids, lennoxamine and chilenine.
authors.affiliation: Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Sendai, Japan. hfuwa@bios.tohoku.ac.jp
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000470:Alkaloids; D000475:Alkenes; D001552:Benzazepines; D002219:Carbamates; D004146:Dioxanes; D004988:Ethers, Cyclic; D006571:Heterocyclic Compounds; D007211:Indoles; C521999:chilenine; C442893:lennoxamine