Abstract
The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry
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Benzofurans / chemical synthesis*
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Benzofurans / chemistry
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Bignoniaceae / chemistry
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Catalysis
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Crystallography, X-Ray
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Furans / chemical synthesis
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Furans / chemistry
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Heterocyclic Compounds, 2-Ring / chemical synthesis
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Heterocyclic Compounds, 2-Ring / chemistry
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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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Stereoisomerism
Substances
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Aldehydes
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Benzofurans
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Furans
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Heterocyclic Compounds, 2-Ring
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Heterocyclic Compounds, 4 or More Rings
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Rengyolone
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incarviditone
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incarvilleatone
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3-hydroxybutanal