Synthesis of l-Kynurenine and Homo-l-Kynurenine via an Aza-Fries Rearrangement

摘要: l -Kynurenine, a non-proteinogenic amino acid, is the primary metabolite of tryptophan via kynurenine pathway. Kynurenine involved in variety biological processes occurring human body, notably central nervous system. Thus, study this molecule offers multiple opportunities for drug discovery; however, an essential prelude studies to secure supply and analogues thereof. A simple synthetic procedure efficient preparation enantiomerically pure -kynurenine from l- aspartic acid its implementation prepare homo- -glutamic presented. The approach relies on photochemical aza-Fries rearrangement corresponding acyl-aniline as fundamental transformation.