Total Synthesis of the Biscarbazole Alkaloids Murrafoline A-D by a Domino Sonogashira Coupling/Claisen Rearrangement/Electrocyclization Reaction.

Angewandte Chemie (International ed. in English)

PubMedID: 24006179

Kumar VP, Gruner KK, Kataeva O, Knölker HJ. Total Synthesis of the Biscarbazole Alkaloids Murrafoline A-D by a Domino Sonogashira Coupling/Claisen Rearrangement/Electrocyclization Reaction. Angew Chem Int Ed Engl. 2013;.
Why take things one step at a time? Aryl-pyran-linked biscarbazole alkaloids of the murrafoline group (see crystal structure of murrafoline A) were accessed readily by a novel domino reaction sequence involving Sonogashira coupling, a Claisen rearrangement, and electrocyclization. The one-pot procedure enables the straightforward synthesis of these structurally challenging alkaloids in only a few steps.