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Paper | Regular issue | Vol 91, No. 4, 2015, pp.782-794
Published online, 18th March, 2015
DOI: 10.3987/COM-15-13188
A Synthesis of Lamellarins via Regioselective Assembly of 1,2,3-Differentially Substituted 5,6-Dihydropyrrolo[2,1-a]Isoquinoline Core

Tsutomu Fukuda, Daichi Sato, and Masatomo Iwao*

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


A modular synthesis of the marine natural products lamellarins has been developed. The key reactions utilized are C3-selective Vilsmeier-Haack formylation followed by iterative bromination/cross-coupling of the 5,6-dihydropyrrolo[2,1-a]isoquinoline core. The 1,2-diaryl-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carbaldehyde thus synthesized was readily converted to the lamellarin skeleton by mean of palladium-catalyzed oxidative lactonization.