UK-2A is a macrocyclic natural product that was isolated from <i>Streptomyces</i> sp. 517-02 found in a soil sample (Osaka University) in 1996. UK-2A was found to possess excellent fungicidal activity, while exhibiting low toxicity towards mammalian cells. UK-2A inhibits mitochondrial electron transport at the ubiquinone Qi site of complex III. This inhibition of ubiquinone reductase at the Qi site (the inner side of the membrane) represents a highly desired new mode of action for the agricultural fungicide market. This presentation will detail the synthesis of picolinamide macrocycles inspired by the fungicidal natural product UK-2A, which we termed the neo-picolinamides. The development of a novel and scalable synthesis of an intermediate used for the rapid preparation of two distinct neo-picolinamide series (X = O, C) will be described.

Divergent approach for the rapid synthesis of picolinamide macrocycles inspired by the fungicidal natural product UK-2A

2019 Spring National Meeting

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