- New Synthesis of Orelline by Metalation of Methoxypyridines
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A new total synthesis in five steps of alkaloid Orelline is reported.The methodology involves metalation of methoxypyridines to afford 2-halo-3,4-dimethoxypyridine on which an homocoupling reaction is performed to build the 2,2'-bipyridyl structure of the
- Trecourt, Francois,Mallet, Marc,Mongin, Olivier,Gervais, Bruno,Queguiner, Guy
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- New syntheses of orelline and analogues via metalation and cross-coupling reactions
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New total syntheses of orelline and some analogues are reported. The methodology involves metalation of 3-alkoxy-2-iodopyridines to afford 3,4-dialkoxy-2-iodopyridines, on which cross-coupling reactions are performed to reach the 2,2′-bipyridine skeleton of the alkaloid.
- Mongin, Florence,Trécourt, Fran?ois,Mongin, Olivier,Quéguiner, Guy
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p. 309 - 314
(2007/10/03)
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- Syntheses of Hydroxylated Bipyridines, I. - Orellanine, the Poison of a Toadstool
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Two syntheses of orellanine, -3,3',4,4'-tetrol-1,1'-dioxide (5b), are developed which comprise 10 or 11 steps, respectively.The chemical reactions of 5b with diazomethane and on UV irradiation are described.
- Dehmlow, Eckehard V.,Schulz, Hans-Joachim
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p. 857 - 862
(2007/10/02)
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- NEW REACTIONS OF PYRIDINES AND TOTAL SYNTHESIS OF THE FUNGAL TOXIN ORELLANINE
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Dihalogenated pyridines react easily with sulphur nucleophiles, in dipolar aprotic solvents (DMF), to afford the products of mono- or of bis-substitution depending on the experimental conditions.On the contrary, with oxygen nucleophiles the bis-substituted products can be obtained only with some particular substrates.A new and efficient procedure to effect the homo-coupling of halogenoarenes will be presented.This reaction, wich occurs under the influence of low-valent nickel complexes, allowed us to effect the total synthesis of Orellanine, the lethal toxin of Cortinarius orellanus mushroom, as well as the syntheses of its decompositionproducts Orellinine and Orelline.The chemical properties of these three products and their behaviour towards UV irradiation will be presented and discussed.
- Tiecco, Marcello
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p. 1009 - 1020
(2007/10/02)
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- SYNTHESIS OF ORELLANINE, THE LETHAL POISON OF A TOADSTOOL
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A ten step synthesis of the structure of orellanine, 3,3',4,4'- hydroxy-2,2'-bipyridyl-bis-N-oxide (1a), is described which proves the identity of the natural product.
- Dehmlow, Eckehard, V.,Schulz, Hans-Joachim
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p. 4903 - 4906
(2007/10/02)
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