Eine neue Synthese von 1,3,4‐Tridesoxy‐1,4‐iminoglyciten mit variabler Kettenlänge durch (C<sub>3</sub> + C<sub>n</sub>)‐Verknüpfung von Allylhalogeniden und Glycononitriloxiden

Müller, Rudolf; Leibold, T.; Pätzel, Michael; Jäger, Volker

doi:10.1002/ange.19941061208

Cited by 15 publications

(4 citation statements)

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“…Die erforderliche Vorstufe 104 war durch Aldoladdition eines a,bungesättigten Aldehyds an den Glycinester 102 zur b-Hydroxyaminosäure 103 und anschließende O-Allylierung zugänglich (Schema 9). [297] Danach wurden die Auswirkungen einer Methylsubstitution an verschiedenen Positionen des Grundgerüsts unter- [299] an 2-Methylfuran [294,300] oder Cyclopentadien erhalten (Schema 10). [301] Leider waren die Anforderungen von Isoleucyl-Aminoacyl-tRNA-Synthetase an die Struktur Furanomycin-ähnli-cher Substrate relativ strikt.…”

Section: Furanomycin Eine Leitstruktur Mit Ungenügen-dem Potenzialunclassified

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: Furanomycin Eine Leitstruktur Mit Ungenügen-dem Potenzialunclassified

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

et al. 2006

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“…The basic set of structures to probe the SAR was complemented by the α‐ S ,2 R ,5 R diastereomer 5′‐ epi ‐furanomycin ( 98 ), 5′‐methylfuranomycin ( 99 ), and L ‐(+)‐dihydrofuranomycin ( 100 ), as well as the carba analogue of the natural antibiotic 101 . These chiral congeners were prepared by 1,3‐dipolar cycloaddition of glyceronitrile oxide as a chiral glycine equivalent299 to either 2‐methylfuran294, 300 or cyclopentadiene (Scheme ) 301…”

Section: Furanomycin a Lead With Insufficient Potentialmentioning

confidence: 99%

Oligothiophene Isothiocyanates as Fluorescent Markers

Barbarella

2002

Chem. Eur. J.

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To create a drug, nature's blueprints often have to be improved through semisynthesis or total synthesis (chemical postevolution). Selected contributions from industrial and academic groups highlight the arduous but rewarding path from natural products to drugs. Principle modification types for natural products are discussed herein, such as decoration, substitution, and degradation. The biological, chemical, and socioeconomic environments of antibacterial research are dealt with in context. Natural products, many from soil organisms, have provided the majority of lead structures for marketed anti‐infectives. Surprisingly, numerous “old” classes of antibacterial natural products have never been intensively explored by medicinal chemists. Nevertheless, research on antibacterial natural products is flagging. Apparently, the “old fashioned” natural products no longer fit into modern drug discovery. The handling of natural products is cumbersome, requiring nonstandardized workflows and extended timelines. Revisiting natural products with modern chemistry and target‐finding tools from biology (reversed genomics) is one option for their revival.

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“…Thus, the erythro-isoxazolidine produced with sodium triacetoxyborohydride on hydrogenation with palladium on carbon as catalyst furnished the erythro-N-methylaminopentanetriol derivative as a pure isomer in 95 % yield [5] [Scheme 10(iii)]. Direct conversion of isoxazolinium salts to give amino alcohols is feasible likewise, as is well-known in the isoxazoline series [22,29,32], albeit with somewhat lower stereoselectivity [Scheme 10, entries (i) and (ii)]. The two-step reduction [entry (iii)] here proved superior.…”

Section: -Isoxazolinium Saltsmentioning

confidence: 99%

2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

Jäger

Frey

Bathich

et al. 2010

Zeitschrift Für Naturforschung B

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Dedicated to Professor Alessandro Dondoni on the occasion of his 75 th birthday2-Isoxazolines represent a well known class of heterocycles, readily accessible in particular by 1,3-dipolar cycloaddition of nitrile oxides to alkenes. 2-Isoxazolines are easily transformed into 2-isoxazolinium salts by N-methylation, and further into 3-isoxazolines by deprotonation. In contrast to the parent system, less is known concerning the chemistry of the derived classes, and potential applications in synthesis. -2-Isoxazolinium salts, due to their iminium part, are prone to the attack of nucleophiles, and examples for this, addition of hydride (reduction) and C-nucleophiles like methylmagnesium bromide, cyanide, methane nitronate, and malonate are given. With these adducts, syntheses of β -and α-amino acids with OH-containing side chains have been effected. The cyanide products also are useful as precursors of branched, unsymmetrical 1,2-diamino polyols. -On the other hand, 3-isoxazolines due to their oxy-enamine part, represent species with nucleophilic sites and therefore react with electrophilic reagents. Examples given are [3+2] cycloadditions with nitrile oxides, [2+2] cycloadditions with dimethyl acetylenedicarboxylate, and [2+1] cycloaddition in the form of epoxidation which, however, led to a dihydro-1,3-oxazine nitrone by initial attack at the nitrogen atom, in an unprecedented oxidation/N-dealkylation/rearrangement sequence.

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Eine neue Synthese von 1,3,4‐Tridesoxy‐1,4‐iminoglyciten mit variabler Kettenlänge durch (C₃ + C_n)‐Verknüpfung von Allylhalogeniden und Glycononitriloxiden

Cited by 15 publications

References 44 publications

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

Oligothiophene Isothiocyanates as Fluorescent Markers

2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

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Eine neue Synthese von 1,3,4‐Tridesoxy‐1,4‐iminoglyciten mit variabler Kettenlänge durch (C3 + Cn)‐Verknüpfung von Allylhalogeniden und Glycononitriloxiden

Cited by 15 publications

References 44 publications

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

Antibakterielle Naturstoffe in der medizinischen Chemie – Exodus oder Renaissance?

Oligothiophene Isothiocyanates as Fluorescent Markers

2-Isoxazolinium Salts and 3-Isoxazolines: Exploratory Chemistry and Uses for the Synthesis of Branched Amino Polyols and Amino Acids

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Eine neue Synthese von 1,3,4‐Tridesoxy‐1,4‐iminoglyciten mit variabler Kettenlänge durch (C₃ + C_n)‐Verknüpfung von Allylhalogeniden und Glycononitriloxiden