Abstract
Reaction of the ethyl 3-arylpyruvate 5a with the methyl 2-bromo-3-arylpyruvate 6b in the presence of the 2-arylethylamine 4 afforded the pyrrole derivative 10, which could be transformed into lamellarin L (1) in five steps. The synthesis proceeds with 38% overall yield and mimics the probable biosynthesis of these marine alkaloids.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis
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Alkaloids / chemistry
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Animals
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry*
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Benzopyrans / chemical synthesis
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Benzopyrans / chemistry*
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Coumarins*
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Heterocyclic Compounds, 4 or More Rings*
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Isoquinolines / chemical synthesis
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Isoquinolines / chemistry*
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Mollusca / chemistry
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Pyrroles / chemistry
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Pyruvates / chemistry*
Substances
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Alkaloids
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Antineoplastic Agents
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Benzopyrans
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Coumarins
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Heterocyclic Compounds, 4 or More Rings
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Isoquinolines
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Pyrroles
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Pyruvates
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lamellarin L