Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization.

Clemes Dialer, Dennis Imbri, Steven Peter Hansen, Till Opatz

The Journal of organic chemistry 2015 Nov 20

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An electrocyclic ring closure of a 2-azapentadienyl anion generated in situ from a chalcone and glycine ester is the key step of an efficient synthesis of the pyrrole core of the lamellarin alkaloids. A recently developed scalable one-pot procedure provides multigram quantities of a 3,5-diaryl-4-iodopyrrole-2-carboxylate intermediate which is transformed in four further high-yielding operations including a one-pot Pomeranz-Fritsch alkylation/cyclization and an Ullmann-type lactone ring closure into the pentacyclic lamellarin skeleton.

Citation

Clemes Dialer, Dennis Imbri, Steven Peter Hansen, Till Opatz. Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization. The Journal of organic chemistry. 2015 Nov 20;80(22):11605-10