Department of Chemistry, Korea University, 145 Anam-ro, Seongbuk-gu, Seoul 02841, Republic of Korea.
J Org Chem. 2020 Jun 19;85(12):8149-8156. doi: 10.1021/acs.joc.0c01051. Epub 2020 Jun 1.
The total synthesis of iheyamine A from readily available ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde is described. The cyanide-catalyzed imino-Stetter reaction of an aldimine derived from ethyl 2-aminocinnamate and 5-methoxyindole-2-carboxaldehyde provided the desired unsymmetrical 2,2'-bisindole-3-acetic acid derivative. The subsequent introduction of an amino group at the C-3' position, followed by the formation of the azepine ring, completed the total synthesis of iheyamine A.
本文描述了从易得的乙基 2-氨基肉桂酸酯和 5-甲氧基吲哚-2-甲醛出发，全合成 iheyamine A。亚胺-斯特勒氰化物催化反应，由乙基 2-氨基肉桂酸酯和 5-甲氧基吲哚-2-甲醛衍生的醛亚胺提供了所需的不对称 2,2'-双吲哚-3-乙酸衍生物。随后在 C-3'位置引入氨基，接着形成氮杂环庚烷环，完成了 iheyamine A 的全合成。
