The regioselective synthesis of aryl pyrroles

Pyrrole is a unique aromatic molecule as it can readily undergo substitution at all five positions but obtaining the desired regioisomer can prove difficult to control. We now report our results on the regioselective arylation of pyrrole, utilizing selective halogenation and the Suzuki - Miyaura reaction to prepare C4-, C5- and C3-aryl derivatives. We have applied this methodology to the synthesis of lamellarin O dimethyl ether, an intermediate in the synthesis of lukinol A.