Diplopyrone is a phytotoxin isolated from the fungus Diplodia mutila and reported by Evidente and coworkers in 2003. D. mutila is considered to be responsible for cork oak decline in parts of southern Europe where the disease has large and negative economic and environmental impacts. The pyranopyran core structure found in diplopyrone also occurs in many other natural products that encompass a range of biological effects including antibiotic activity. Viewing diplopyrone as a “C-glycoside problem” opens up multiple synthetic routes that are based on carbohydrate starting materials. We have been exploring carbon-carbon bond forming reactions that utilize glycosyl sulfones, nitriles, and vinyl glycosides in our efforts to synthesize enantiomeric, (-)-diplopyrone from D-glucose and D-galactose. Three analogs have been synthesized and assayed for phytotoxic activity using a leaf puncture assay.

C-Glycosyl compounds in the synthesis of analogs of the phytotoxin diplopyrone

254th National Meeting (2017)

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