Total Synthesis and Neuritotrophic Activity of Farinosone C and Derivatives

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.