Abstract
(+)-Grandifloracin was synthesized from sodium benzoate by means of a dearomatizing dihydroxylation that proceeds with unusual regioselectivity. Iron diene complexes formed from the arene oxidation product permit the use of otherwise inaccessible transformations. The synthetic material was shown to be antipodal to the natural product, thus determining the absolute configuration of grandifloracin for the first time.
© 2011 American Chemical Society
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Bridged-Ring Compounds / chemical synthesis*
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Bridged-Ring Compounds / chemistry
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Bridged-Ring Compounds / isolation & purification
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Catalysis
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Cyclohexenes / chemical synthesis
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Cyclohexenes / chemistry
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Iron
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Molecular Structure
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Oxidation-Reduction
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Sodium Benzoate / chemistry*
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Stereoisomerism
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Uvaria / chemistry
Substances
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Bridged-Ring Compounds
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Cyclohexenes
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grandifloracin
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Iron
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Sodium Benzoate