Abstract
Canthin-6-one (1) and nine analogues including the naturally occurring 9-methoxycanthin-6-one (2) and amaroridine (3) are prepared rapidly and in high yields via a convergent "non-classical" strategy that focuses on construction of the central ring B. The strategy relies on concomitant Pd-catalyzed Suzuki-Miyaura C-C coupling followed by a Cu-catalyzed C-N coupling that can be achieved either stepwise or in a new one-pot protocol starting from the appropriate 8-bromo-1,5-naphthyridine.
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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Amides / chemical synthesis*
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Amides / chemistry
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Carbolines
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Catalysis
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Copper / chemistry*
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Indole Alkaloids
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Indoles / chemical synthesis*
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Indoles / chemistry
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Molecular Structure
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Naphthyridines / chemical synthesis*
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Naphthyridines / chemistry
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Organometallic Compounds / chemistry*
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Palladium / chemistry*
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Stereoisomerism
Substances
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Alkaloids
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Amides
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Carbolines
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Indole Alkaloids
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Indoles
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Naphthyridines
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Organometallic Compounds
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canthin-6-one
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Palladium
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Copper