Abstract
The first syntheses of the Phomopsis-isolated natural products phochrodines A-C are reported. Functional group manipulations on a key 5H-chromeno[4,3-b]pyridine intermediate, itself synthesized from intramolecular Suzuki-Miyaura coupling, enabled facile and high-yielding syntheses of all three natural products. Additionally, sufficient material was generated to enable detailed pharmacological profiling of each compound. Preliminary drug metabolism and pharmacokinetic (DMPK) experiments and ancillary pharmacology screening revealed phochrodine C (3) as an attractive scaffold for further modification, particularly for medicinal chemists working in the antidepressant space.