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

Autor:	Anastasia Kharlamova, Jonathan E. Hempel, John T. Gupton, Keith Krumpe, Raymond N. Dominey, James A. Sikorski, Bradley K. Norwood, Barrett A. Little, Anthony Diebes, Shahnaz Ghassemi, Rene P.F. Kanters, Edith J. Banner, Charles R. Hickenboth, Matthew B. Coppock, Herman L. Holt, Bruce S. Burnham, Austin B. Scharf, Karen X. Du, Kartik M. Keertikar, Itta Bluhn-Chertudi, Melissa D. Sartin
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Organic Chemistry Salt (chemistry) Halogenation Iminium Biochemistry Acylation Hydrolysis chemistry.chemical_compound chemistry Drug Discovery Organic chemistry Curtius rearrangement Pyrrole
Zdroj:	Tetrahedron. 62:8243-8255
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.06.047
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b6e8e5631e95a30844cd36fe9b3a78ac https://doi.org/10.1016/j.tet.2006.06.047 Zobrazit plný text záznamu Full Text from ScienceDirect