title: A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine.
abstract: Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University Mainz , Duesbergweg 10-14, Mainz D-55128, Germany.
authors.forename: Nicola
authors.initials: N
authors.lastname: Otto
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University Mainz , Duesbergweg 10-14, Mainz D-55128, Germany.
authors.forename: Dorota
authors.initials: D
authors.lastname: Ferenc
authors.affiliation: Institute of Organic Chemistry, Johannes Gutenberg-University Mainz , Duesbergweg 10-14, Mainz D-55128, Germany.
authors.forename: Till
authors.identifier: 0000-0002-3266-4050
authors.initials: T
authors.lastname: Opatz
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003300:Copper / Q000737:chemistry; D007546:Isoquinolines / Q000737:chemistry*; D015394:Molecular Structure; D014403:Tubocurarine / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001547:Benzaldehydes; D007546:Isoquinolines; C470478:curine; D003300:Copper; C100058:vanillin; D014403:Tubocurarine