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Synfacts 2018; 14(03): 0221
DOI: 10.1055/s-0037-1609241
DOI: 10.1055/s-0037-1609241
Synthesis of Natural Products and Potential Drugs
Concise Synthesis of the Alkaloid (±)-Aspergilline A
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
15. Februar 2018 (online)
Key words
aspergilline A - anti-cancer activity - tobacco mosaic virus - tetramic acid derivatives - indole alkaloidsSignificance
Aspergilline A was isolated from the fungus Aspergillus versicolor and possesses activity against the tobacco mosaic virus as well as anti-cancer activity. The Wood group reports a synthesis relying on an elegant pyrrolinone formation and a formal [3+2] cycloaddition.
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Comment
Acylation followed by addition to an alkyne and double-bond isomerization transforms C into E. Mukaiyama aldol reaction creates the core structure in F. Imidate G undergoes formal cycloaddition with cyclopropenone to form I which is further transformed into the indole alkaloid aspergilline A through an oxidation–acetalization–decarboxylation sequence.
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