The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether.
The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether.
复制标题
溴吡咯酯的甲酰基活化在番茄红素C、全甲基斯托尼酰胺A和板层素G三甲醚的形式合成中的应用。
DOI：
10.1016/j.tet.2014.11.035
复制
发表时间：
2014
期刊：
影响因子：
2.1
通讯作者：
Curry,Will
中科院分区：
文献类型：
--
作者：
Gupton,JohnT;Telang,Nakul;Patteson,Jon;Lescalleet,Kristin;Yeudall,Scott;Sobieski,John;Harrison,Andrew;Curry,Will
番茄红素C、全甲基三甲胺A和板蓝素G三甲醚是含有吡咯的天然产物，具有许多有趣的生物学特性。这些特性包括在各种癌细胞系上的抗肿瘤活性，包括那些具有耐药性的细胞，抑制艾滋病毒整合酶和血管破坏活性。我们现在描述了3-溴-2-甲酰基吡咯-5-羧酸甲酯和乙基吡咯-5-羧酸乙酯的用途，为这三个高度官能化的生物活性吡咯的正式合成奠定了基础。由于能够容易地修改吡咯核心的位置2、3、4和5，这些新的构建块现在将提供对天然产品和许多新的类似物的容易访问。
Lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether are pyrrole containing, natural products, which exhibit interesting biological properties. Such properties include anti-tumor activity on a variety of cancer cell lines including those that confer drug resistance, inhibition of HIV integrase and vascular disrupting activity. We now describe the use of methyl and ethyl 3-bromo-2-formylpyrrole-5-carboxylate as building blocks for the formal synthesis of these three highly functionalized, bioactive pyrroles. These new building blocks will now provide ready access to the natural products and many novel analogs due to the ability to easily modify positions 2,3,4 and 5 of the pyrrole core.