Hiroya Kou, Matsumoto Shigemitsu, Sakamoto Takao
Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-ku, Sendai 980-8578, Japan.
Org Lett. 2004 Aug 19;6(17):2953-6. doi: 10.1021/ol0489548.
The sequential coupling and cyclization reactions between aryl halides and methyl propiolate were investigated. The electron-withdrawing groups on the aromatic ring are essential for producing the methyl indole-2-carboxylate derivatives. On the other hand, the presence of an extra methyl propiolate and Pd(PPh3)4 were required to provide an efficient catalytic system for the cyclization reactions. This reaction was used for the total synthesis of duocarmycin SA.
研究了芳基卤化物与丙酸甲酯之间的顺序偶联和环化反应。芳环上的吸电子基团对于生成吲哚 -2- 羧酸甲酯衍生物至关重要。另一方面，需要额外的丙酸甲酯和 Pd(PPh3)4 的存在来提供用于环化反应的高效催化体系。该反应被用于多卡霉素 SA 的全合成。
