An efficient construction of the central 1,2,4-trisubstituted pyrrole core via one-pot [3+2] cycloaddition/elimination/aromatization sequence-based domino process and subsequent Pd-mediated cross dehydrogenative coupling between the C-H bonds of pyrrole and the peripheral aryl rings enables rapid access to the pentacyclic coumarin-pyrrole-isoquinoline scaffolds which were smoothly elaborated to the targeted lamellarins alkaloids. The total synthesis of lamellarins Z and S with the highest overall yield reported till date, besides the synthesis of several other natural lamellarins have been realized in 5-6 steps with overall yields ranging from 20-27%.
Keywords: aziridine; cross-dehydrogenative coupling; domino process; lamellarins; total synthesis
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Kumar, V.; Salam, A.; Kumar, D.; Khan, T. Beilstein Arch. 2020, 202087. doi:10.3762/bxiv.2020.87.v1
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