Title
The Application Of Vinylogous Iminium Salt Derivatives To An Efficient Synthesis Of The Pyrrole Containing Alkaloids Rigidin And Rigidin E
Keywords
Marine natural product; Microwave acceleration; Pyrrole; Vinamidinium salt
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. © 2006 Elsevier Ltd. All rights reserved.
Publication Date
8-28-2006
Publication Title
Tetrahedron
Volume
62
Issue
35
Number of Pages
8243-8255
Document Type
Article
Personal Identifier
scopus
DOI Link
https://doi.org/10.1016/j.tet.2006.06.047
Copyright Status
Unknown
Socpus ID
33745950883 (Scopus)
Source API URL
https://api.elsevier.com/content/abstract/scopus_id/33745950883
STARS Citation
Gupton, John T.; Banner, Edith J.; Scharf, Austin B.; Norwood, Bradley K.; and Kanters, Rene P.F., "The Application Of Vinylogous Iminium Salt Derivatives To An Efficient Synthesis Of The Pyrrole Containing Alkaloids Rigidin And Rigidin E" (2006). Scopus Export 2000s. 8016.
https://stars.library.ucf.edu/scopus2000/8016