Abstract
An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz-Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Anions / chemistry*
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Coumarins / chemical synthesis*
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Coumarins / chemistry
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Cyclization
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Ethers / chemistry*
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Isoquinolines / chemical synthesis*
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Isoquinolines / chemistry
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Molecular Structure
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Pyrroles / chemical synthesis
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Pyrroles / chemistry*
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Stereoisomerism
Substances
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Anions
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Coumarins
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Ethers
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Heterocyclic Compounds, 4 or More Rings
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Isoquinolines
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Pyrroles
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lamellarin D
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lamellarin H