Abstract
A short and practical synthesis of oseltamivir was accomplished in 11 steps from inexpensive and abundant diethyl D-tartrate starting material. This azide-free route featured an asymmetric aza-Henry reaction and a domino nitro-Michael/Horner-Wadsworth-Emmons (HWE) reaction as the key steps to construct the relevant cyclohexene ring of the product, which provided an economical and practical alternative for the synthesis of oseltamivir.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antiviral Agents / chemical synthesis*
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Cyclization
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Cyclohexenes / chemistry
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Enzyme Inhibitors / chemical synthesis*
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Humans
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Influenza A Virus, H5N1 Subtype / enzymology
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Molecular Structure
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Neuraminidase / antagonists & inhibitors*
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Oseltamivir / chemical synthesis*
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Tartrates / chemistry*
Substances
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Antiviral Agents
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Cyclohexenes
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Enzyme Inhibitors
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Tartrates
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cyclohexene
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Oseltamivir
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Neuraminidase
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diethyl tartrate