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Paper | Special issue | Vol 93, No. 2, 2016, pp.593-612
Published online, 5th October, 2015
DOI: 10.3987/COM-15-S(T)49
Regioselective Synthesis of 2,4-Differentially Arylated Pyrroles and Its Application to The Synthesis of Lamellarins

Tsutomu Fukuda, Mizuho Anzai, and Masatomo Iwao*

*Division of Chemistry and Materials Science, Graduate School of Engineering, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

An efficient method for the synthesis of 2,4-differentially arylated pyrroles has been developed via stepwise palladium-catalyzed Suzuki–Miyaura coupling of N-benzenesulfonyl-4-bromo-2-iodopyrrole with different arylboronic acids. This method has been applied to the new synthesis of the marine natural products lamellarins.