Issue 9, 2024

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
21 Jan 2024
Accepted
18 Feb 2024
First published
23 Feb 2024

Org. Chem. Front., 2024,11, 2433-2441

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

Z. Xu, X. Liang, P. Lan and M. G. Banwell, Org. Chem. Front., 2024, 11, 2433 DOI: 10.1039/D4QO00131A

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