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Paper | Special issue | Vol 95, No. 2, 2017, pp.950-971
Published online, 16th February, 2017
DOI: 10.3987/COM-16-S(S)63
Synthesis of Lamellarins via Regioselective Assembly of 1,2-Diarylated [1]Benzopyrano[3,4-b]pyrrol-4(3H)-one Core

Tsutomu Fukuda,* Takatoshi Katae, Issei Harada, 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 lamellarins has been developed. The key reactions in this synthesis are the assembly of 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones from a preexisting [1]benzopyrano[3,4-b]pyrrol-4(3H)-one core and the appropriate arylboronic acids. The obtained 1,2-diarylated [1]benzopyrano[3,4-b]pyrrol-4(3H)-ones could be easily converted into the corresponding lamellarin derivatives by intramolecular annulation between the pyrrole nitrogen and the C2 aromatic ring.