726187-74-2Relevant academic research and scientific papers
Electrooxidation based strategy towards the core 3-amino-6-hydroxy-azepan- 2-one
David, Marc,Dhimane, Hamid
, p. 1029 - 1033 (2004)
We describe a practical synthesis of protected (3S,6R)-6-hydroxy- cyclolysine derivatives starting from cyclic L-lysine. Evaluation of the electrochemical oxidation of various protected amino-caprolactams allowed a regioselective electromethoxylation at the α-position to the lactam nitrogen. Formation of the corresponding enamide by elimination of methanol followed by a diastereoselective dihydroxylation, diacetylation and subsequent regioselective reduction afford the orthogonally protected (3S,6R)-3-amino-6- hydroxy-azepan-2-one.
