The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products |
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Authors: | 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 |
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Institution: | a Department of Chemistry, University of Richmond, Richmond, VA 23173, USA b AtheroGenics Inc., 8995 Westside Parkway, Alpharetta, GA 30004, USA |
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Abstract: | 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. |
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Keywords: | Vinamidinium salt Pyrrole Marine natural product Microwave acceleration |
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