Abstract
We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Bridged-Ring Compounds / chemical synthesis*
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Bridged-Ring Compounds / chemistry
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Carbon / chemistry
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Cyanates / chemistry
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Cyclization
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Isocyanates / chemistry
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Nitrogen / chemistry
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Piperidines / chemical synthesis*
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Piperidines / chemistry
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Stereoisomerism
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Substrate Specificity
Substances
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Alkaloids
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Bridged-Ring Compounds
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Cyanates
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Isocyanates
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Piperidines
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adaline
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euphococcinine
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Carbon
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Nitrogen