title: First total synthesis of dioxepine bastadin 3.
abstract: The synthesis of dioxepine bastadin 3, a tyrosine-tyramine derivative with a dibenzo-1,3-dioxepine scaffold that is rarely present among natural products, is described. The dibenzo-1,3-dioxepine ring was formed early in the sequence and the (E)-2-(hydroxyimino)-N-alkylamide was generated in the last step by oxidation of the 2-amino-N-alkylamide precursor. The presumably biogenetic late-stage ring formation starting from congener bastadin 3 failed. A new synthesis of this alkaloid was also developed. This new route requires a minimal use of protecting groups and the order of the two key steps was reversed relative to the route to dioxepine bastadin 3.
authors: Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain.
authors: Santiago
authors: S
authors: Pérez-Rodríguez
authors: Raquel
authors: R
authors: Pereira-Cameselle
authors: Angel R
authors: AR
authors: de Lera
mesh_terms: D000588:Amines / Q000737:chemistry; D001584:Benzoxepins / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003990:Dibenzoxepins / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D014439:Tyramine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000588:Amines; D001584:Benzoxepins; D003990:Dibenzoxepins; D014439:Tyramine