Abstract
A concise (9-step) synthesis of the tropoloisoquinoline alkaloid pareitropone has been achieved starting from 2-bromoisovanillin. The key step features oxidative cyclization of a readily available phenolic nitronate for the convenient construction of the fused tropone ring. This work underscores the synthetic utility of intramolecular oxidative coupling reactions of phenolic nitronates.
Publication types
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Research Support, N.I.H., Extramural
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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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Anions
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Benzaldehydes / chemistry*
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Hydrocarbons, Brominated / chemistry*
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Isoquinolines / chemical synthesis*
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Isoquinolines / chemistry
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Molecular Structure
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Oxidation-Reduction
Substances
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2-bromoisovanillin
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Alkaloids
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Anions
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Benzaldehydes
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Hydrocarbons, Brominated
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Isoquinolines
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pareitropone