Synthesis of labionin and avionin precursors via a nitrogen-centred-radical-triggered 1,5-HAT reaction of Tris derivatives

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논문

Synthesis of labionin and avionin precursors via a nitrogen-centred-radical-triggered 1,5-HAT reaction of Tris derivatives

학술지

Organic & biomolecular chemistry

저자명

Yamaguchi, Ayuta; Obiya, Naoki; Arichi, Norihito; Oishi, Shinya; Ohno, Hiroaki; Inuki, Shinsuke

초록

Labionin and avionin are non-proteinogenic amino acids containing 2,4-diamino-2-(mercaptomethyl)pentanedioic acid that forms the core structures of spirocyclic peptides including labyrinthopeptin A2 and microvionin, respectively. We have developed a diastereoselective synthetic route to labionin and avionin precursors. This route highlights the formation of the quaternary carbon stereocenter of an α,α-disubstituted amino acid via a regioselective 1,5-HAT reaction of a Tris derivative.Graphic AbstractIn this study, we have developed a diastereoselective synthetic route to labionin and avionin precursors via a regioselective 1,5-HAT reaction of Tris derivatives. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=d3ob02037a'/>

발행연도

2024

발행기관

The Royal Society of Chemistry

ISSN

1477-0520

ISSN

1477-0539

권

호

페이지

pp.2049-2055