An efficient method for the synthesis of enol ethers and enecarbamates. Total syntheses of isoindolobenzazepine alkaloids, lennoxamine and chilenine.
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.
Fuwa
Haruhiko
H
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Sendai, Japan. hfuwa@bios.tohoku.ac.jp
Sasaki
Makoto
M
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
D000470:Alkaloids; D000475:Alkenes; D001552:Benzazepines; D002219:Carbamates; D004146:Dioxanes; D004988:Ethers, Cyclic; D006571:Heterocyclic Compounds; D007211:Indoles; C521999:chilenine; C442893:lennoxamine