Abstract
Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Alkylation
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Crystallography, X-Ray
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Cyclization
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Indole Alkaloids
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Indoles / chemical synthesis*
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Indoles / chemistry
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Models, Molecular
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Molecular Structure
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Nitriles / chemical synthesis*
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Nitriles / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Indole Alkaloids
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Indoles
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Nitriles
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welwitindolinone A
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welwitindolinone B
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welwitindolinone C isothiocyanate