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Total Syntheses of the Linearly-Fused Prenylated Indole Alkaloids Asperversiamides H and M via Oxidative Rearrangement of the Putative Biosynthetic Precursor Dihydrocarneamide A
European Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2025-04-15 , DOI: 10.1002/ejoc.202500277
Xinru Li Zhongnan Xu Shenting Zhang Wenzhu Yu Shen Tan Martin G. Banwell

A new synthesis of the linearly-fused prenylated indole alkaloid dihydrocarneamide A is reported and on treatment of this with a peracid it undergoes oxidative fragmentation to give a previously unreported isomer of the natural product amoenamide A. In contrast, treatment of dihydrocarneamide A with an oxaziridine afforded a mixture of the oxindole-containing natural products asperversiamides H and M.

中文翻译:

亚麻融合异戊二烯基化吲哚生物碱 Asperversiamides H 和 M 通过假定的生物合成前体二氢卡奈酰胺 A 的氧化重排进行全合成

报道了线性熔合的异戊二烯基化吲哚生物碱二氢卡奈酰胺 A 的新合成,在用过酸处理后,它发生氧化碎裂,得到以前未报道的天然产物阿米酰胺 A 的异构体。相比之下,用恶嗪啶处理二氢卡奈酰胺 A 提供了含氧吲哚的天然产物曲霉酰胺 H 和 M 的混合物。
更新日期:2025-04-15
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