A novel sequential aminodiene Diels-Alder strategy for the rapid construction of substituted analogues of Kornfeld's ketone.
A novel sequential aminodiene Diels-Alder strategy for the rapid construction of substituted analogues of Kornfeld's ketone.
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DOI：
10.1021/ol0268992
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发表时间：
2002-10
期刊：
影响因子：
5.2
通讯作者：
S. Bur;A. Padwa
中科院分区：
文献类型：
--
作者：
S. Bur;A. Padwa
通过一系列新的氨基二烯Diels-Alder反应，酰胺基呋喃18 a-c以中等至良好的产率转化为三环酮21 a-c。酮21 a可通过裂解氨基甲酸叔丁酯并氧化除去甲酯转化为乌勒酮（6）。三氯甲烷21 a容易地进行溴化，得到22。形成相应的烯醇三氟甲磺酸酯25，然后羰基化，得到酯27，然后将其与N-甲基丙酰胺偶联，得到26。[反应：见正文]
Through a novel sequence of aminodiene Diels-Alder reactions, amidofurans 18a-c were converted to tricyclic ketones 21a-c in moderate to good yields. Ketone 21a could be converted to Uhlé's ketone (6) by cleaving the tert-butyl carbamate and oxidatively removing the methyl ester. Tricycle 21a readily underwent bromination to give 22. Formation of the corresponding enol triflate 25 followed by carbonylation gave ester 27, which was then coupled with N-methyl propriolamide to furnish 26. [reaction: see text]