Abstract
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.
Key words
bengamides - diastereoselectivity - dihydroxylation - electrooxidation - osmium
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