Brønsted Acid Catalyzed One-Pot Benzannulation of 2-Alkenylindoles under Aerial Oxidation: A Route to Carbazoles and Indolo[2,3-a]carbazole Alkaloids,Organic Letters

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Brønsted Acid Catalyzed One-Pot Benzannulation of 2-Alkenylindoles under Aerial Oxidation: A Route to Carbazoles and Indolo[2,3-a]carbazole Alkaloids
Organic Letters ( IF 4.9 ) Pub Date : 2018-10-25 00:00:00 , DOI: 10.1021/acs.orglett.8b03063
Shuvendu Saha ₁ , Ankush Banerjee ₁ , Modhu Sudan Maji ₁

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A one-pot, protecting-group-free benzannulation of 2-alkenylindoles with readily available 1,3-dicarbonyls is demonstrated to construct structurally diverse carbazoles. The use of a cheap Brønsted acid catalyst and air as the sole oxidant exemplifies the economic viability of this protocol. The execution of four different reactions successively to generate the medicinally important indolocarbazole core is also achieved. This one-pot protecting-group-free method paved the way for the total synthesis of three medicinally important alkaloids, namely staurosporinone, arcyriaflavin A, and 7-hydroxy-K252c.

中文翻译：

空气氧化作用下布朗斯台德酸催化2-烯基吲哚的一锅苯环化反应：生成咔唑和吲哚并[2,3- a ]咔唑生物碱的途径

具有容易获得的1，3-二羰基的一锅，无保护基的2-烯基吲哚的苯环被证明可构建结构多样的咔唑。使用廉价的布朗斯台德酸催化剂和空气作为唯一氧化剂证明了该方案的经济可行性。还实现了依次进行四个不同反应以产生具有医学重要性的吲哚并咔唑核。这种一锅法式的无保护基方法为全合成三种医学上重要的生物碱铺平了道路，所述生物碱是星形孢菌素，反式黄酮A和7-羟基-K252c。

更新日期：2018-10-25

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