Gupton John T, Banner Edith J, Sartin Melissa D, Coppock Matthew B, Hempel Jonathan E, Kharlamova Anastasia, Fisher Daniel C, Giglio Ben C, Smith Kristin L, Keough Matt J, Smith Timothy M, Kanters Rene P F, Dominey Raymond N, Sikorski James A
Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
Tetrahedron. 2008;64(22):5246-5253. doi: 10.1016/j.tet.2008.03.038.
Studies directed at the synthesis of polycitone and storniamide natural products via vinylogous iminium salts and microwave accelerated Vilsmeier-Haack formylations are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 2,3,4-trisubstituted pyrrole from a vinamidinium salt or vinamidinium salt derivative followed by formylation at the 5-position of the pyrrole. Subsequent transformations of the selectively formylated pyrroles lead to efficient and regiocontrolled relay syntheses of the respective pyrrole containing natural products.
本文描述了通过烯醇亚胺盐和微波加速的Vilsmeier-Haack甲酰化反应合成聚柠檬酸和斯托尼亚胺天然产物的研究。成功的策略依赖于由脒鎓盐或脒鎓盐衍生物形成2,4-二取代吡咯或2,3,4-三取代吡咯，随后在吡咯的5-位进行甲酰化。选择性甲酰化吡咯的后续转化导致了相应含吡咯天然产物的高效和区域可控的接力合成。
