Abstract
The formal synthesis of (+)-3-epi-eupomatilone-6 () and the 3,5-bis-epimer () has been accomplished. The key synthetic strategy involved the stereoselective construction of (3R,4S,5R)- and (3R,4S,5S)-trisubstituted γ-butyrolactones and from (2R,3R)-2,3-dimethyl-4-pentenoic acid derivative , which was readily obtained via stereoselective conjugate addition of vinylmagnesium chloride to a chiral α,β-unsaturated N-acyl oxazolidinone (Evans' auxiliary) followed by α-methylation.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Chemistry, Pharmaceutical / methods*
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Chlorides / chemistry
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Drug Design
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Hydrocarbons, Iodinated / chemistry
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Lactones / chemistry
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Magnesium Chloride / chemistry
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Magnetic Resonance Spectroscopy
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Methylation
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Molecular Structure
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Plant Extracts / chemistry
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Stereoisomerism
Substances
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Benzofurans
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Chlorides
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Hydrocarbons, Iodinated
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Lactones
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Plant Extracts
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eupomatilone-6
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Magnesium Chloride
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methyl iodide