A flexible approach to ethyl (3R,4S)-N-Boc-4-amino-3-hy-droxy-5-phenyIpentanoate (N-Boc-AHPPA-OEt), the γ-amino-β-hydroxy add moiety of hapalosin is described. The synthetic method features a ring-opening ethanolysi...A flexible approach to ethyl (3R,4S)-N-Boc-4-amino-3-hy-droxy-5-phenyIpentanoate (N-Boc-AHPPA-OEt), the γ-amino-β-hydroxy add moiety of hapalosin is described. The synthetic method features a ring-opening ethanolysis of an activated N-Boc-lactam, which is obtained via a diastereoselective reductive-alkylation of (R)-malimide derivative. The flexibility of the method resides hi the introduction of the alkyl side chain by Grignard reagent addition.展开更多
基金Project supported by the National Science Foundation for Distinguished Young Investigators,the National Natural Science Foundation of China and the Fund for doctoral sites of the Ministry of Education.
文摘A flexible approach to ethyl (3R,4S)-N-Boc-4-amino-3-hy-droxy-5-phenyIpentanoate (N-Boc-AHPPA-OEt), the γ-amino-β-hydroxy add moiety of hapalosin is described. The synthetic method features a ring-opening ethanolysis of an activated N-Boc-lactam, which is obtained via a diastereoselective reductive-alkylation of (R)-malimide derivative. The flexibility of the method resides hi the introduction of the alkyl side chain by Grignard reagent addition.
