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Two Synthesis Approaches of the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System of Alchivemycins A and B
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2023-12-20 , DOI: 10.1002/ejoc.202301006 Osamu Ishibashi 1 , Yasuhiro Meguro 1 , Shigefumi Kuwahara 1 , Masaru Enomoto 2
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2023-12-20 , DOI: 10.1002/ejoc.202301006 Osamu Ishibashi 1 , Yasuhiro Meguro 1 , Shigefumi Kuwahara 1 , Masaru Enomoto 2
Affiliation
The 2H-tetrahydro-4,6-dioxo-1,2-oxazine (TDO) ring model of alchivemycins, an unprecedented structural motif in natural products, was synthesized via two routes. Both routes involved the intramolecular trapping of an acylketene intermediate by an internal hydroxy group as a key step. A DMAP−CaCl2-mediated O- to C-acyl migration reaction enabled installation of an acyl group at the C5 position of an unstable TDO intermediate.
中文翻译:
Alchivemycins A和B 2H-四氢-4,6-二氧代-1,2-恶嗪环系的两种合成方法
阿尔奇维霉素的2 H -四氢-4,6-二氧代-1,2-恶嗪 (TDO) 环模型是天然产物中前所未有的结构基序,通过两种途径合成。两条路线都涉及通过内部羟基对酰基乙烯酮中间体进行分子内捕获作为关键步骤。DMAP-CaCl 2介导的O-至C-酰基迁移反应使得能够在不稳定的TDO中间体的C5位置安装酰基。
更新日期:2023-12-20
中文翻译:
Alchivemycins A和B 2H-四氢-4,6-二氧代-1,2-恶嗪环系的两种合成方法
阿尔奇维霉素的2 H -四氢-4,6-二氧代-1,2-恶嗪 (TDO) 环模型是天然产物中前所未有的结构基序,通过两种途径合成。两条路线都涉及通过内部羟基对酰基乙烯酮中间体进行分子内捕获作为关键步骤。DMAP-CaCl 2介导的O-至C-酰基迁移反应使得能够在不稳定的TDO中间体的C5位置安装酰基。