Total synthesis of (±)-martinellic acid
Total synthesis of (±)-martinellic acid
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DOI：
10.1021/ol016884o
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发表时间：
2001-12-27
期刊：
影响因子：
5.2
通讯作者：
O'Hare, SM
中科院分区：
文献类型：
--
作者：
Snider, BB;Ahn, Y;O'Hare, SM
[图表]通过苯胺 11 与 Meldrum 的酸活化乙烯基环丙烷 4 反应生成乙烯基吡咯烷酮 12，醛 13 与 N-苄基甘氨酸缩合形成偶氮甲碱叶立德，环化生成 14，选择性还原 14 为氨基醇，完成了马丁尼酸 (1) 的 14 步合成，总产率为 3% 16 用 LiBH4 和 MeOH，以及通过氰胺与 3-甲基-2-丁烯-1-胺在六氟-2-丙醇中于 120℃反应形成胍作为关键步骤，
[GRAPHICS]A 14-step synthesis of martinellic acid (1) that proceeds in 3% overall yield has been completed using the reaction of aniline 11 with Meldrum's acid-activated vinylcyclopropane 4 to give vinyl pyrrolidinone 12, condensation of aldehyde 13 with N-benzylglycine to form an azomethine ylide that cyclizes to give 14, selective reduction of 14 to amino alcohol 16 with LiBH4 and MeOH, and guanidine formation by reaction of a cyanamide with 3-methyl-2-buten-1-amine in hexafluoro-2-propanol at 120 degreesC as key steps,