The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E
Abbreviated Journal Title
vinamidinium salt; pyrrole; marine natural product; microwave; acceleration; MARINE NATURAL-PRODUCTS; RELAY SYNTHESIS; POLYCITONE-A; AMINES; Chemistry, Organic
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. (c) 2006 Elsevier Ltd. All rights reserved.
"The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E" (2006). Faculty Bibliography 2000s. 6186.