The protecting group manoeuvring as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol (12a) and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol (22) in the domino synthesis of benzofuran-based natural products (1–8). The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M (1) and cicerfuran (2), and the first time synthesis of moracin D (3) and moracin E (4) along with chromene-fused benzofuran-based natural products (5–8) in overall good yields.

中文翻译：

---

调节官能团的稳定性和反应性：合成西呋喃，草胶（D，E，M）和色烯稠合的基于苯并呋喃的天然产物

应用操纵基团作为策略来调节4-（2,2-二溴乙烯基）苯-1,3-二醇（12a）和6-（2,2-二溴乙烯基）-2,2-的稳定性和反应性基于苯并呋喃的天然产物（1-8）的多米诺合成中的二甲基苯并吡喃-7-醇（22）。在钯催化条件下，通过在多米诺偶联反应中用取代的宝石-二溴乙烯基苯酚和三芳基铋试剂改变保护基，可以成功地控制官能团的要求及其对电子效应的反应性。这种方法为合成moracin M（1）和cicerfuran（2），以及首次合成moracin D（3）铺平了道路。）和莫拉辛E（4）以及基于色烯稠合的苯并呋喃的天然产物（5-8），总体上具有良好的产量。