The application of vinylogous iminium salt derivatives to an efficient synthesis of the pyrrole containing alkaloids Rigidin and Rigidin E

• Published in: Tetrahedron Vol. 62; no. 35; pp. 8243 - 8255
• Main Authors: Gupton, John T., Banner, Edith J., Scharf, Austin B., Norwood, Bradley K., Kanters, Rene P.F., Dominey, Raymond N., Hempel, Jonathan E., Kharlamova, Anastasia, Bluhn-Chertudi, Itta, Hickenboth, Charles R., Little, Barrett A., Sartin, Melissa D., Coppock, Matthew B., Krumpe, Keith E., Burnham, Bruce S., Holt, Herman, Du, Karen X., Keertikar, Kartik M., Diebes, Anthony, Ghassemi, Shahnaz, Sikorski, James A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.08.2006; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Marine natural product; Microwave acceleration; Physical Sciences; Pyrrole; Science & Technology; Vinamidinium salt; Vinamidinium salt; Marine natural product; Microwave acceleration; Pyrrole; POLYCITONE-A; AMINES; microwave acceleration; RELAY SYNTHESIS; marine natural product; MARINE; vinamidinium salt; pyrrole
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2006.06.047

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. [Display omitted]