Synthesis and Bioactivity of a Macrocidin B Stereoisomer.

Weber, Stefanie E; Gaß, Juliane; Zeng, Haoxuan; Erb-Brinkmann, Maike; Schobert, Rainer

dc.contributor.author	Weber, Stefanie E
dc.contributor.author	Gaß, Juliane
dc.contributor.author	Zeng, Haoxuan
dc.contributor.author	Erb-Brinkmann, Maike
dc.contributor.author	Schobert, Rainer
dc.date.accessioned	2021-11-26T12:31:40Z
dc.date.available	2021-11-26T12:31:40Z
dc.date.issued	2021-10-11
dc.identifier.citation	Org Lett. 2021 Nov 5;23(21):8273-8276. doi: 10.1021/acs.orglett.1c03013. Epub 2021 Oct 11.	en_US
dc.identifier.pmid	34633201
dc.identifier.doi	10.1021/acs.orglett.1c03013
dc.identifier.uri	http://hdl.handle.net/10033/623102
dc.description.abstract	A stereoisomer of macrocidin B, a presumed metabolite of the fungus Phoma macrostoma, was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was N-β-ketoacylated with a fully functionalized octanoyl Meldrum's acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macrocyclized via Williamson etherification between the phenol and epi-bromohydrin termini. This macrocidin B stereoisomer showed a weaker herbicidal effect than macrocidin A and no similar inhibitory effect on biofilms of Staphylococcus aureus.	en_US
dc.language.iso	en	en_US
dc.publisher	ACS	en_US
dc.rights	Attribution 4.0 International	*
dc.rights.uri	http://creativecommons.org/licenses/by/4.0/	*
dc.title	Synthesis and Bioactivity of a Macrocidin B Stereoisomer.	en_US
dc.type	Article	en_US
dc.identifier.eissn	1523-7052
dc.contributor.department	HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.	en_US
dc.identifier.journal	Organic letters	en_US
dc.source.volume	23
dc.source.issue	21
dc.source.beginpage	8273
dc.source.endpage	8276
dc.source.journaltitle	Organic letters
dc.source.country	United States