Total syntheses of certain asperversiamides, linearly-fused and prenylated indole alkaloids

Biogenetically patterned total syntheses of the prenylated indole alkaloids asperversiamides B, D, E, G and J as well as dihydrocarneamide A have been realised while a related synthesis of the racemic modification of the structure assigned to asperversiamide A suggests this is incorrect. The efficie...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-04, Vol.11 (9), p.2433-2441
Main Authors: Xu, Zhongnan, Xin-Ting, Liang, Lan, Ping, Banwell, Martin G
Format: Article
Language:English
Subjects:
Alkaloids
Natural products
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Summary:Biogenetically patterned total syntheses of the prenylated indole alkaloids asperversiamides B, D, E, G and J as well as dihydrocarneamide A have been realised while a related synthesis of the racemic modification of the structure assigned to asperversiamide A suggests this is incorrect. The efficient oxidative rearrangement of (±)-asperversiamide D into the C8a′ epimer of asperversiamide C suggests this spiro-oxindole is likely to be a natural product-in-waiting as is ent-asperversiamide F, the co-product from the Stryker-type reduction of asperversiamide G.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo00131a