Abstract
The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine-2,3-dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross-coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biological Products / chemical synthesis*
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Biological Products / chemistry*
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Catalysis
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Catecholamines / chemistry*
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Cyclization
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry*
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / chemistry*
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Indoleamine-Pyrrole 2,3,-Dioxygenase / antagonists & inhibitors*
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Indoleamine-Pyrrole 2,3,-Dioxygenase / chemistry*
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Indoles / chemical synthesis*
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Indoles / chemistry*
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Molecular Structure
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Quinones / chemical synthesis*
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Quinones / chemistry*
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry*
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Stereoisomerism
Substances
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Biological Products
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Catecholamines
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Enzyme Inhibitors
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Indole Alkaloids
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Indoleamine-Pyrrole 2,3,-Dioxygenase
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Indoles
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Quinones
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Spiro Compounds
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exiguamine A
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exiguamine B