Department of Chemistry MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Org Lett. 2010 Jun 4;12(11):2664-7. doi: 10.1021/ol100896n.
The synthesis of (+/-)-eusynstyelamide A has been accomplished in six steps in 13% overall yield from 6-bromoindole, methyl glycidate, and Boc-protected agmatine. If oxygen is carefully excluded from the reaction, the key NaOH-catalyzed aldol dimerization of the alpha-ketoamide proceeded efficiently to give Boc-protected eusynstyelamide A.
(±)-eusynstyelamide A 的合成为 6-溴吲哚、甲基甘油酸酯和 Boc 保护的胍基乙酸六步反应,总收率为 13%。如果在反应中小心地排除氧气,关键的 NaOH 催化的 α-酮酰胺的羟醛缩合反应就能有效地进行,得到 Boc 保护的 eusynstyelamide A。