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Aza-BODIPY Route to Ageladine A
Christian Tolle1, Marvin Fresia1, Thomas Lindel1
1TU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany.
Abstract:
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.
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