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An efficient synthesis of all four possible stereoisomers of the neurotrophic amide farinosone C was developed. The absolute and relative configuration was assigned by comparison of synthetic material with a derivatized authentic sample of the natural product. Several derivatives allowed for the generation of preliminary structure activity relationships concerning neurite outgrowth in PC-12 cells, unravelling l-tyrosinol-amide as the pharmacophore.
Giovanni De Micheli, Mathias Soeken, Winston Jason Haaswijk
Nicolai Cramer, Daria Grosheva