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

Ohsawa, Kosuke, Zhao, Hongbin, Tokunaga, Takuya, Thomas, Carys, Ganesan, A. ORCID: https://orcid.org/0000-0003-4862-7999, Masuda, Yuichi and Doi, Takayuki (2020) Stereoselective synthesis of protected l-allo-Enduracididine and l-Enduracididine via asymmetric nitroaldol reaction. Synthesis-Stuttgart, 52 (6). pp. 942-948. ISSN 0039-7881

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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 (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Related URLs:	http://www.scopus.com/inward/record.url?... http://www.thieme-connect.de/DOI/DOI?10....
Depositing User:	LivePure Connector
Date Deposited:	20 Feb 2020 07:53
Last Modified:	25 Sep 2024 14:26
URI:	https://ueaeprints.uea.ac.uk/id/eprint/74259
DOI:	10.1055/s-0039-1691522

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