Total synthesis of orellanine : The lethal toxin of Cortinarius Orellanus fries mushroom |
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| Institution: | 1. UCIBIO, REQUIMTE, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto (FFUP), 4050-313 Porto, Portugal;2. UCIBIO, REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 404169-007 Porto, Portugal;3. UCIBIO, REQUIMTE, Instituto de Ciências Biomédicas de Abel Salazar, Universidade do Porto, 4050-313 Porto, Portugal;1. Department of Surgery, University of Virginia, Charlottesville;2. Department of Surgery, University of Florida, Gainesville;1. Chemistry Research Laboratory, HMS Institute of Technology, NH-4, Kyathasandra, Tumakuru, Karnataka, India;2. Channabasaveshwara Institute of Technology, Gubbi, Tumakuru District, Tumakuru, Karnataka, India;2. i3S - Instituto de Investigação e Inovação em Saúde, Universidade do Porto, Portugal;3. IBMC-Instituto de Biologia Molecular e Celular, 4150-180 Porto, Portugal;4. ICBAS- Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Portugal |
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| Abstract: | The syntheses of the main toxin of Cortinarius Orellanus Fries, orellanine, and of its decomposition product, orelline, are reported. The structures of 3,3',4,4'-tetrahydroxy-2,2'-bipyridyl-N,N'-dioxide for orellanine and of 3,3',4,4'-tetrahydroxy-2,2'-bipyridyl for orelline have been proposed by W.Z. Antkowiak and W.P. Gessner. These two conpounds have now been synthesized starting from the 3,3',4,4'-tetramethoxy-2,2'-bipyridyl which could be obtained in good yields by the nickel-phosphine complex-mediated homo coupling of 2-bromo-3,4-dimethoxy pyridine according to the general procedure previously reported by us. The 3,3',4,4'-tetrahydroxy-2,2'-bipyridyl was obtained by demethylation with hydrobromic acid. The oxidation of this compound with hydrogen peroxide afforded the 3,3',4,4'-tetrahydroxy-2,2'-bipyridyl-N,N'-dioxide. This latter compound was also obtained by the demethylation of the 3,3',4,4'-tetramethoxy-2,2'-bipyridyl-N,N'-dioxide with hydrobromic acid. The products obtained presented physical and spectral properties identical to those of the natural products. |
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