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The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E |
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| Authors: | John T Gupton Edith J Banner Bradley K Norwood Raymond N Dominey Anastasia Kharlamova Charles R Hickenboth Melissa D Sartin Keith E Krumpe Herman Holt Kartik M Keertikar Shahnaz Ghassemi |
| Institution: | a Department of Chemistry, University of Richmond, Richmond, VA 23173, USA b Department of Chemistry, University of North Carolina at Asheville, Asheville, NC 28804, USA c Department of Chemistry, University of Central Florida, Orlando, FL 32816, USA d Biotage Inc., 1725 Discovery Drive, Charlottesville, VA 22911, USA e AtheroGenics Inc., 8995 Westside Parkway, Alpharetta, GA 30004, USA |
| Abstract: | Studies directed on the synthesis of the pyrrole containing marine natural products Rigidin and Rigidin E via vinylogous iminium salts are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole from a vinamidinium salt followed by acylation at the 5-position of pyrrole. Halogenation and aminocarbonylation at the 3-position of pyrrole followed by hydrolysis of the ester group at C-2 and subsequent Curtius rearrangement generates the pyrrolopyrimidine skeleton. A final deprotection step completes the synthesis of Rigidin and Rigidin E. |
| Keywords: | Vinamidinium salt Pyrrole Marine natural product Microwave acceleration |
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