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The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C,permethyl storniamide A and lamellarin G trimethyl ether
Institution:1. School of Advanced Materials Science and Engineering, Changwon National University, Changwon, Gyeongman 641-773, Republic of Korea;2. Technical Research Laboratories Pohang Research Lab., Steelmaking Research Group, POSCO, Pohang, Gyeongbuk 790-300, Republic of Korea
Abstract: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.
Keywords:Suzuki cross-coupling  Pyrrole  Marine natural products
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