Abstract
Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-μ-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Benzopyrans / chemical synthesis*
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Biological Products / chemical synthesis*
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Copper / chemistry*
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Copper / metabolism
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Isoquinolines / chemical synthesis*
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Methylation
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Models, Molecular
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Molecular Structure
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Oxidation-Reduction
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Oxygen / chemistry
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Pyridones / chemistry
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Sparteine / chemistry*
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Stereoisomerism
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Temperature
Substances
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8-O-methylsclerotiorinamine
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Benzopyrans
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Biological Products
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Isoquinolines
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Pyridones
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Sparteine
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Copper
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sclerotiorin
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Oxygen