The Snyder lab has successfully achieved the first total synthesis of chalcitrin, a rare natural compound that is a striking yellow pigment found in the peppery bolete mushroom (Chalciporous piperatus). While these mushrooms grow worldwide in mixed woodland ecosystems, when they have been found in abundance near smelting factories or in the Chernobyl nuclear disaster zone, where the soil is high in radioactive cesium, they possess extremely high levels of metal ions. Chalcitrin is a unique polyphenol that might be responsible for that finding, as it and some of its structural cousins readily bind alkali metal ions. In "The Total Synthesis of Chalcitrin," published in the Journal of the American Chemical Society on February 27, 2019, the Snyder group delineates a 17-step laboratory synthesis of chalcitrin using commercially available materials to fashion its unique architectural elements. Several of the developed operations may assist in the preparation and biological evaluation of other unique mushroom pigments.
By Irene Hsiao