Abstract
A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki-Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Boronic Acids / chemical synthesis*
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Boronic Acids / chemistry
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / chemistry
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Isoindoles / chemistry*
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Lactams / chemical synthesis*
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Lactams / chemistry
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Molecular Structure
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Phenanthrenes / chemical synthesis*
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Phenanthrenes / chemistry
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Plant Extracts / chemical synthesis*
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Plant Extracts / chemistry
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Stereoisomerism
Substances
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Aldehydes
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Alkaloids
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Boronic Acids
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Indole Alkaloids
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Isoindoles
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Lactams
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Phenanthrenes
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Plant Extracts
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aristolactam BII
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piperolactam A
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sauristolactam
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3-hydroxybutanal