First total synthesis of caerulomycin K: a case study on selective, multiple C-H functionalizations of pyridines

Caerulomycins, natural alkaloids with antimicrobial properties, have been previously synthesized starting with highly pre-functionalized building blocks or requiring many functional group manipulations. In this work, we report the first total synthesis of caerulomycin K, a diversely trifunctionalized pyridine readily assembled in three steps exploiting the recent advancements in the C-H activation of N-heterocycles. A radical change: the first 3-steps total synthesis of caerulomycin K was achieved exploiting Minisci chemistry using cheap starting materials.