Abstract
Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Biomimetic Materials / chemical synthesis*
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Biomimetic Materials / chemistry
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Catecholamines* / biosynthesis
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Catecholamines* / chemical synthesis
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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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Indoles / chemical synthesis*
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Indoles / chemistry
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Molecular Structure
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Oxidation-Reduction
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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
Substances
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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