125134-29-4Relevant articles and documents
1-Hydroxy-3-amino-2-piperidone (δ-N-Hydroxycycloornithine) Derivatives: Key Intermediates for the Synthesis of Hydroxamate-Based Siderophores
Kolasa, Teodozyj,Miller, Marvin J.
, p. 1711 - 1721 (2007/10/02)
Several routes for the synthesis of δ-N-(benzyloxy)cycloornithine (2) from glutamic acid derived starting materials are described.Efficient methods were developed for the synthesis of glutamic acid γ-semialdehyde and γ-hydroxynorvaline derivatives as key substrates for the preparation of δ-N-hydroxyornithine analogues.Thus, the best approaches to the synthesis of 2 were: (1) reductive cyclization of an N-hydroxysuccinimide ester of the O-benzyloxime 4 of α-amino-protected glutamic acid γ-semialdehyde 5 and (2) cyclization of the N-(benzyloxy)amide of δ-bromonorvaline (7).