Highly Efficient Chiral-Pool Synthesis of (2<i>S</i>,4<i>R</i>)-4-Hydroxyornithine

Rudolph, Joachim; Hannig, Frithjof; Theis, and Heidi; Wischnat, Ralf

doi:10.1021/ol016445p

Cited by 39 publications

(32 citation statements)

References 29 publications

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“…[347] Über alternative Ansätze zu unterschiedlich geschützten Hydroxyornithin-Derivaten wurde bereits andernorts berichtet. [348] Die Schutzgruppenmanipulation und Aktivierung der Säureeinheit als Pentafluorphenylester 175 (für die Makrocylisierung) gelang in ausgezeichneten Ausbeuten in einem Zweiphasensystem unter Hochverdünnungsbedingungen. Nach gleichzeitigem Entfernen von fünf Schutzgruppen wurde schließlich 21 erhalten (Schema 16).…”

Section: Biphenomycineunclassified

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

et al. 2006

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Zur Entwicklung von Medikamenten müssen die Strukturvorlagen aus der Natur oft durch Semisynthese oder Totalsynthese verbessert werden (chemische Post‐Evolution). Der Weg vom Naturstoff zum Arzneimittel ist mühsam aber lohnenswert. Die grundlegenden Typen der chemischen Naturstoffmodifikation – Dekoration, Substitution und Abbau – werden hier besprochen, und das biologische, chemische und sozioökonomische Umfeld antibakterieller Forschung wird betrachtet. Naturstoffe waren und bleiben die ergiebigste Leitstrukturquelle für vermarktete Antiinfektiva, und obwohl viele lange bekannte Klassen nie grundlegend erforscht worden sind, erlahmen die industrielle wie die akademische Forschung auf diesem Gebiet – die “altmodischen” Naturstoffe scheinen nicht mehr ins Bild der modernen Wirkstoff‐Forschung zu passen, ihre Handhabung ist aufwändig und erfordert oft nichtstandardisierte Prozesse und längere Bearbeitungszeiten. Eine Neubetrachtung von Naturstoffen mit Methoden der modernen Chemie und Biologie (Reversed Genomics) könnte ihre Renaissance in der Arzneimittelforschung einleiten.

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Section: Biphenomycineunclassified

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

et al. 2006

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“…Where necessary, flash column chromatography was performed on silica gel 60 (230 ± 400 mesh). Except for alcohols 18,20,22,24,26,28,30,34,36, and 38 all starting compounds are commercially available. Alcohols 22, 24, and 26 were prepared from commercial (2R)-3-hydroxy-2-methylpropionic methyl ester by standard protection of the alcohol group and dibalpromoted reduction of the ester functionality under standard conditions.…”

Section: Methodsmentioning

confidence: 99%

“…Recently, we communicated on the use of the polymer-supported bisacetoxybromate(I) anion 6. [21,22] Among the different modes of attachment of active species to a polymer, ion exchange is probably best suited for regeneration. In this report, we give a detailed account on this reagent system which includes its scopes and limitations.…”

Section: Introductionmentioning

confidence: 99%

Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols

2003

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A polymer-bound reagent for the efficient oxidation of primary alcohols to aldehydes and secondary alcohols to ketones in the presence of a catalytic amount of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) is described. The oxidation process is particular mild and allows one to prepare aldehydes with a-chirality without racemization. This also includes the synthesis of a-aminoaldehydes. In most cases, work-up of this heavy metal-free oxidation is achieved by simple filtration followed by removal of the solvent. Insight into the role of the bromate(I) anion in the oxidation process was gained from the TEMPO-mediated oxidation of benzaldehyde in the presence of the hypochlorite anion loaded on an anion exchange resin.

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“…The synthesis of L-allo-enduracididine ( 3 ) was reported to begin with nitro alcohol 61 and afforded the free amino acid in four steps via key intermediate 4-hydroxyarginine 62 . The synthesis of nitro alcohol 61 was not described but its preparation has been reported [65]. All four diastereomers were synthesised for comparison with the isolated enduracididine sample.…”

Section: Reviewmentioning

confidence: 99%

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

Atkinson¹,

Naysmith²,

Furkert³

et al. 2016

Beilstein J. Org. Chem.

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Rising resistance to current clinical antibacterial agents is an imminent threat to global public health and highlights the demand for new lead compounds for drug discovery. One such potential lead compound, the peptide antibiotic teixobactin, was recently isolated from an uncultured bacterial source, and demonstrates remarkably high potency against a wide range of resistant pathogens without apparent development of resistance. A rare amino acid residue component of teixobactin, enduracididine, is only known to occur in a small number of natural products that also possess promising antibiotic activity. This review highlights the presence of enduracididine in natural products, its biosynthesis together with a review of analogues of enduracididine. Reported synthetic approaches to the cyclic guanidine structure of enduracididine are discussed, illustrating the challenges encountered to date in the development of efficient synthetic routes to facilitate drug discovery efforts inspired by the discovery of teixobactin.

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Highly Efficient Chiral-Pool Synthesis of (2S,4R)-4-Hydroxyornithine

Cited by 39 publications

References 29 publications

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

Polymer‐Supported Bisacetoxybromate(I) Anion –‐An Efficient Co‐Oxidant in the TEMPO‐Mediated Oxidation of Primary and Secondary Alcohols

Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis

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