Abstract
[Structure: see text] An efficient one-step synthetic protocol for 3-methyl-5-bromo-2-pyrone was developed using the C3-selective Pd-catalyzed coupling reaction of 3,5-dibromo-2-pyrone with Me3Al-dimethylaminoethanol complex. A subsequent seven-step reaction sequence provided a cyclohexenyl bromide, which served as the key intermediate for the synthesis of the keto analogue of phomactin A, in 31% overall yield.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aluminum / chemistry
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Catalysis
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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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Molecular Structure
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Organometallic Compounds / chemistry
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Palladium / chemistry*
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Pyrones / chemistry*
Substances
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3-methyl-5-bromo-2-pyrone
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Heterocyclic Compounds, 4 or More Rings
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Organometallic Compounds
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Pyrones
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phomactin A
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Palladium
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Aluminum