Abstract
A synthesis of the steroidal alkaloid demissidine from epiandrosterone is reported. A ring fragmentation reaction that efficiently ruptured the D-ring of a diazo ester derivative of epiandrosterone to provide an aldehyde tethered ynoate product was key to this sequence. Incorporation of the indolizidine framework was achieved by an azomethine ylide 1,3-dipolar cycloaddition.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry
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Crystallography, X-Ray
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Cycloaddition Reaction
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Indolizidines / chemistry*
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Solanaceous Alkaloids / chemical synthesis*
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Solanaceous Alkaloids / chemistry
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Stereoisomerism
Substances
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Alkaloids
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Indolizidines
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Solanaceous Alkaloids
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demissidine