Abstract
A convergent total synthesis of the marine natural product dysiherbaine was accomplished. The key steps of the synthesis are an alkylation at the gamma-carbon of a protected glutamate with a highly substituted pyran derived from mannose, which was followed by a ring-contraction cascade reaction, which simultaneously gave the tetrasubstituted carbon and the hexahydrofuro[3,2-b]pyran ring system of the natural product.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alanine / analogs & derivatives*
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Alanine / chemical synthesis*
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Alanine / chemistry
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Alkylation
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Biological Factors / chemical synthesis*
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Biological Factors / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Catalysis
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Chemistry, Organic / methods*
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oxidation-Reduction
Substances
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Biological Factors
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Bridged Bicyclo Compounds, Heterocyclic
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dysiherbaine
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Alanine