e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Total synthesis of orellanine: The lethal toxin of Cortinarius Orellanus fries mushroom

M Tiecco, M Tingoli, L Testaferri, D Chianelli…

Index: Tiecco; Tingoli; Testaferri; et al. Tetrahedron, 1986 , vol. 42, # 5 p. 1475 - 1485

Full Text: HTML

Citation Number: 52

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 WZ Antkowiak and WP Gessner. These two conpounds have now been synthesized starting from the 3, 3', 4, 4'-tetramethoxy-2, 2'-bipyridyl which could be ...

Pyridin-3-ol Structure

~%

orellanine Structure

3-Pyridinol 1-oxide Structure

3-Pyridinol 1-oxide

~%

orellanine Structure

2-Brompyridin-3-ol Structure

2-Brompyridin-3-ol

~%

orellanine Structure

2-Bromo-3-methoxypyridine Structure

2-Bromo-3-metho...

~%

orellanine Structure

N/A Structure

~%

orellanine Structure

3-hydroxy-2-(3-hydroxy-4-oxo-1H-pyridin-2-yl)-1H-pyridin-4-one Structure

3-hydroxy-2-(3-...

~87%

orellanine Structure

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

~83%

2-(3,4-dimethoxy-1-oxidopyridin-2-ylidene)-3,4-dimethoxypyridin-1-ium 1-oxide Structure

2-(3,4-dimethox...

Pyridin-3-ol Structure

~%

2-(3,4-dimethoxy-1-oxidopyridin-2-ylidene)-3,4-dimethoxypyridin-1-ium 1-oxide Structure

2-(3,4-dimethox...

3-Pyridinol 1-oxide Structure

3-Pyridinol 1-oxide

~%

2-(3,4-dimethoxy-1-oxidopyridin-2-ylidene)-3,4-dimethoxypyridin-1-ium 1-oxide Structure

2-(3,4-dimethox...

2-Brompyridin-3-ol Structure

2-Brompyridin-3-ol

~%

2-(3,4-dimethoxy-1-oxidopyridin-2-ylidene)-3,4-dimethoxypyridin-1-ium 1-oxide Structure

2-(3,4-dimethox...

2-Bromo-3-methoxypyridine Structure

2-Bromo-3-metho...

~%

2-(3,4-dimethoxy-1-oxidopyridin-2-ylidene)-3,4-dimethoxypyridin-1-ium 1-oxide Structure

2-(3,4-dimethox...

N/A Structure

~%

2-(3,4-dimethoxy-1-oxidopyridin-2-ylidene)-3,4-dimethoxypyridin-1-ium 1-oxide Structure

2-(3,4-dimethox...

orellanine Structure

~51%

3-hydroxy-2-(3-hydroxy-4-oxo-1H-pyridin-2-yl)-1H-pyridin-4-one Structure

3-hydroxy-2-(3-...

3-Pyridinol 1-oxide Structure

3-Pyridinol 1-oxide

~%

3-hydroxy-2-(3-hydroxy-4-oxo-1H-pyridin-2-yl)-1H-pyridin-4-one Structure

3-hydroxy-2-(3-...

2-Bromo-3-methoxypyridine Structure

2-Bromo-3-metho...

~%

3-hydroxy-2-(3-hydroxy-4-oxo-1H-pyridin-2-yl)-1H-pyridin-4-one Structure

3-hydroxy-2-(3-...

N/A Structure

~%

3-hydroxy-2-(3-hydroxy-4-oxo-1H-pyridin-2-yl)-1H-pyridin-4-one Structure

3-hydroxy-2-(3-...

3-Pyridinol 1-oxide Structure

3-Pyridinol 1-oxide

~71%

2-Bromo-3-pyridinol-1-oxide Structure

2-Bromo-3-pyrid...

2,6-dibromo-3-hydroxypyridine N-oxide Structure

2,6-dibromo-3-h...

Pyridin-3-ol Structure

~%

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

3-Pyridinol 1-oxide Structure

3-Pyridinol 1-oxide

~%

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

2-Brompyridin-3-ol Structure

2-Brompyridin-3-ol

~%

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

2-Bromo-3-methoxypyridine Structure

2-Bromo-3-metho...

~%

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

N/A Structure

~%

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

diazomethane Structure

2-(3-Hydroxy-4-methoxypyridin-2-yl)-4-methoxypyridin-3-ol Structure

2-(3-Hydroxy-4-...

~%

3,3',4,4'-Tetramethoxy-2,2'-bipyridine Structure

3,3',4,4'-Tetra...

Synthesis of orellanine the lethal poison of a toadstool

[Dehmlow, Eckehard, V.; Schulz, Hans-Joachim Tetrahedron Letters, 1985 , vol. 26, # 40 p. 4903 - 4906]

Synthesis of orellanine the lethal poison of a toadstool

[Dehmlow, Eckehard, V.; Schulz, Hans-Joachim Tetrahedron Letters, 1985 , vol. 26, # 40 p. 4903 - 4906]