Tetrahedron

The application of vinylogous iminium salt derivatives to an efficient relay synthesis of the pyrrole containing alkaloids polycitone A and B

…, KM Keertikar, NE Lauerman, JM Solano, BR Adams…

Index: Gupton, John T.; Miller, Robert B.; Krumpe, Keith E.; Clough, Stuart C.; Banner, Edith J.; Kanters, Rene P.F.; Du, Karen X.; Keertikar, Kartik M.; Lauerman, Nicholas E.; Solano, John M.; Adams, Bret R.; Callahan, Daniel W.; Little, Barrett A.; Scharf, Austin B.; Sikorski, James A. Tetrahedron, 2005 , vol. 61, # 7 p. 1845 - 1854

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Citation Number: 31

Abstract

A new and efficient relay synthesis of the marine natural products polycitone A and B is described. The new strategy relies on the formation of 2, 4-disubstituted pyrroles from a vinamidinium salt followed by electrophilic substitution at the 5-position of the pyrrole and Suzuki coupling at the 4-position to produce the tetrasubstituted heterocycle efficiently and with complete control of regiochemistry.