Aza-BODIPY Route to Ageladine A.

The marine natural product ageladine A was synthesized by exploiting novel aza-BODIPY-type boron complexes that allowed the regioselective dibromination of the pyrrole unit, as confirmed by quantum chemical calculation (ωB97XD/TApr-cc-pVDZ). The parent tricycle was accessed by Suzuki-Miyaura cross-coupling employing Buchwald's precatalyst. The boron complex of ageladine A exhibited strong fluorescence that was greater than that of the natural product by a factor of ∼30 and that disappeared in the presence of 2-azido groups.