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

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

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-pos...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron Vol. 61; no. 7; pp. 1845 - 1854
Main Authors: 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.
Format: Journal Article
Language:English
Published: Elsevier Ltd 14-02-2005
Subjects:
Marine natural product
Pyrrole
Vinamidinium salt
Marine natural product
Vinamidinium salt
Pyrrole
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.12.015