Stereoselective synthesis of protected l-allo-Enduracididine and l-Enduracididine via asymmetric nitroaldol reaction

Ohsawa, Kosuke, Zhao, Hongbin, Tokunaga, Takuya, Thomas, Carys, Ganesan, A., Masuda, Yuichi and Doi, Takayuki (2020) Stereoselective synthesis of protected l-allo-Enduracididine and l-Enduracididine via asymmetric nitroaldol reaction. Synthesis, 52 (6). pp. 942-948. ISSN 0039-7881

Full text not available from this repository. (Request a copy)

Abstract

The diastereoselecetive and scalable synthesis of cyclic guanidine-containing nonproteinoginic amino acids, enduracididines, has been achieved. Both diastereomers, l-allo-enduracididine and l-enduracididine, were prepared via catalyst-controlled asymmetric nitroaldol reaction with the aldehyde precursor derived from l-aspartic acid. The cyclic guanidine of di-Cbz-protected l-allo-enduracididine was fully protected with an allyl group to suppress nucleophilic side reactions. Introduced allyl group was efficiently removed via π-allylpalladium chemistry without attaching the Cbz group on the cyclic guanidine moiety.

Item Type: Article
Uncontrolled Keywords: amino-acid,antibacterial,component,peptide,substitution,teixobactin analogs,asymmetric nitroaldol reactions,cyclic guanidines,enduracididines,guanidine functionalization,nonproteinogenic amino acids
Faculty \ School: Faculty of Science > School of Pharmacy
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 20 Feb 2020 07:53
Last Modified: 18 Sep 2020 23:49
URI: https://ueaeprints.uea.ac.uk/id/eprint/74259
DOI: 10.1055/s-0039-1691522

Actions (login required)

View Item View Item