Polybrominated aromatics, such as polybrominated diphenyl ethers (PBDEs) and their derivatives dibenzo-p-dioxins have attracted attention due to their toxicity. The origin of such compounds in the marine environment has been ambiguous because some PBDEs and their derivatives have been shown to be natural products while the majority of PBDEs are produced industrially as flame retardants. Recently isolated from Pseudoalteromonas collected from nudibranchs, 2,3,5,7-tetrabromobenzofuro[3,2-b]pyrrole (TBFP) has shown anti-MRSA (methicillin resistant Stahphylococcus aureus) activities and possesses 3-phenoxypyrrole ether linkage similar to dibenzo-p-dioxins. To elucidate TBFP’s biogenesis and to provide a facile access to this anti-MRSA compound with a novel scaffold, a bio-inspired chemical synthesis and a biocatalytic synthesis of TBFP are pursued. To this end, the putative biosynthetic precursor for TBFP, pentabromopsuedilin was synthesized in two-steps utilizing the MIDA boronate ester Suzuki-Miyaura coupling. For the chemical approach, modification of the Ullmann-type coupling reactions is investigated to allow for a low temperature nucleophile substitution of 3-bromopyrrole. For the latter biocatalytic approach, we employ the cytochrome P450 enzyme involved in the biosynthesis of pentabromopseudilin to cause the phenolic cyclization onto the pyrrole ring. Herein reported are our progress toward these complementary approaches to TBFP as well as the lessons learned along the way.

Bio-inspired chemistry for synthesis of a polybrominated pyrrole marine alkaloid with antibacterial properties

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.