Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Org Lett. 2013 Jun 7;15(11):2644-7. doi: 10.1021/ol400904y. Epub 2013 May 10.
Syntheses of two 6,12-guaianolide analogs are reported within. The scope of the tandem allylboration/lactonization chemistry is expanded to provide a functionalized allene-yne-containing α-methylene butyrolactone that undergoes a Rh(I)-catalyzed cyclocarbonylation reaction to afford a 5-7-5 ring system. The resulting cycloadducts bear a structural resemblance to other NF-κB inhibitors such as cumambrin A and indeed were shown to inhibit NF-κB signaling and cancer cell growth.
本文报道了两种 6,12-愈创木内酯类似物的合成。该串联烯丙基硼化/内酯化化学的范围得到扩展，提供了一种含功能化的烯丙基-炔的α-亚甲基丁内酯，该内酯经历 Rh(I)催化的环羰化反应，得到一个 5-7-5 环系统。所得的环加成物与其他 NF-κB 抑制剂（如 cumambrin A）具有相似的结构，并且确实显示出抑制 NF-κB 信号和癌细胞生长的作用。
