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Synthesis of the Four Diastereoisomers of the N-Terminal Amino Acids of Nikkomycins via Aminoalkylation with Preformed Ternary Iminium Salts
-
Jeanne Delbos-Krampe
und
Ulrich Flörke
Veröffentlicht/Copyright:
2. Juni 2014
Abstract
An efficient and convenient two step synthesis of each of the four possible diastereoisomers of the N-terminal amino acid component of nikkomycins is described. We first synthesized α-amino-β-oxo acids by aminoalkylation of ketones with iminium salts. The second step using Pearlman’s catalyst gave directly nonnatural and natural precursors 13 - 16 of nikkomycins 1 which were easily separated by chromatography on silica gel.
Received: 2004-1-13
Published Online: 2014-6-2
Published in Print: 2004-4-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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Artikel in diesem Heft
- Chemistry of Iminium Salts and Related Compounds
- Orthoamide, LX [1]. N,N,N’,N’-Tetraformylhydrazin – ein breit anwendbares Formylierungsmittel für aromatische Verbindungen / Orthoamide, LX [1]. N,N,N’,N’-Tetraformylhydrazine – a Formylation Agent for Aromatic Compounds of Wide Scope
- Die Synthese von 2-Methyl-5-phenacyl-1,3,4-thiadiazolen / The Synthesis of 2-Methyl-5-phenacyl-1,3,4-thiadiazoles
- Absolute Konfiguration von (+)-1,2,3,4,6,7,8,8a-Octahydro-6-isochinolon- 8a-carbonsäuremethylester und die Stereochemie einer Kupfer-katalysierten asymmetrischen Michael-Reaktion / Absolute Configuration of Methyl (+)-1,2,3,4,6,7,8,8a-Octahydro-6-isoquinolone-8a-carboxylate and Stereochemistry of a Copper-Catalyzed Asymmetric Michael Reaction
- Reactions of Quinolizine- and Pyridino[1,2–a]pyrimidine-3-diazonium Tetrafluoroborates with Aliphatic Amines
- Fries Rearrangement of Aryl Formates Promoted by BCl3. Mechanistic Evidence from 11B NMR Spectra and DFT Calculations
- C-Branched Glycals as Monosaccharidic Push-Pull Butadienes
- 1,4,5,8-Tetraazafulvalene – Darstellung schwefelhaltiger Derivate und Zuordnung des Chromophors / 1,4,5,8-Tetraazafulvalenes – Synthesis of Sulfur-Containing Derivatives and Classification of the Chromophor
- Synthesis of the Four Diastereoisomers of the N-Terminal Amino Acids of Nikkomycins via Aminoalkylation with Preformed Ternary Iminium Salts
- Reactions of 3-Chloropropeniminium Salts with Aminopyridines. Synthesis of N-Pyridylpyridinium and Pyrido[1,2-a]pyrimidinium Salts
- A New Efficient Synthesis of Substituted Luminols Using Multicomponent Reactions
- Preparation and Characterisation of N,N-Disubstituted 2-Amino-5H-selenophenes
- The Coupling-Isomerization Approach to Enimines and the First Sequential Three-Component Access to 2-Ethoxy Pyridines
- Isoxazolinium Salts in Asymmetric Synthesis. 1. Stereoselective Reduction Induced by a 3’-Alkoxy Stereocentre. A New Approach to Polyfunctionalized β-Amino Acids* [1, 2]
- Enantioselective Synthesis of Epi-Emetine Analogues: Control of the Facial Selectivity in a Three-Component Domino Knoevenagel-Hetero-Diels-Alder Reaction*
- Facile Synthesis of Novel N-Aryl-4,5,6,7-tetrahydro-benzosultams by Oxyfunctionalisation of Bicyclic Isothiazolium Salts*
- Reactivity of Tetracyclic Iminium Salts of the Benzo[f]pyrido[2,1-a]- isoindole and Azepino[2,1-a]benzo[f]isoindole Type, with a Preliminary Analysis of their Interactions with Nucleic Acids*
Schlagwörter für diesen Artikel
Nikkomycins;
Mannich Bases;
Aminoalkylation;
Lactones;
1,3-Amino Alcohols
Artikel in diesem Heft
- Chemistry of Iminium Salts and Related Compounds
- Orthoamide, LX [1]. N,N,N’,N’-Tetraformylhydrazin – ein breit anwendbares Formylierungsmittel für aromatische Verbindungen / Orthoamide, LX [1]. N,N,N’,N’-Tetraformylhydrazine – a Formylation Agent for Aromatic Compounds of Wide Scope
- Die Synthese von 2-Methyl-5-phenacyl-1,3,4-thiadiazolen / The Synthesis of 2-Methyl-5-phenacyl-1,3,4-thiadiazoles
- Absolute Konfiguration von (+)-1,2,3,4,6,7,8,8a-Octahydro-6-isochinolon- 8a-carbonsäuremethylester und die Stereochemie einer Kupfer-katalysierten asymmetrischen Michael-Reaktion / Absolute Configuration of Methyl (+)-1,2,3,4,6,7,8,8a-Octahydro-6-isoquinolone-8a-carboxylate and Stereochemistry of a Copper-Catalyzed Asymmetric Michael Reaction
- Reactions of Quinolizine- and Pyridino[1,2–a]pyrimidine-3-diazonium Tetrafluoroborates with Aliphatic Amines
- Fries Rearrangement of Aryl Formates Promoted by BCl3. Mechanistic Evidence from 11B NMR Spectra and DFT Calculations
- C-Branched Glycals as Monosaccharidic Push-Pull Butadienes
- 1,4,5,8-Tetraazafulvalene – Darstellung schwefelhaltiger Derivate und Zuordnung des Chromophors / 1,4,5,8-Tetraazafulvalenes – Synthesis of Sulfur-Containing Derivatives and Classification of the Chromophor
- Synthesis of the Four Diastereoisomers of the N-Terminal Amino Acids of Nikkomycins via Aminoalkylation with Preformed Ternary Iminium Salts
- Reactions of 3-Chloropropeniminium Salts with Aminopyridines. Synthesis of N-Pyridylpyridinium and Pyrido[1,2-a]pyrimidinium Salts
- A New Efficient Synthesis of Substituted Luminols Using Multicomponent Reactions
- Preparation and Characterisation of N,N-Disubstituted 2-Amino-5H-selenophenes
- The Coupling-Isomerization Approach to Enimines and the First Sequential Three-Component Access to 2-Ethoxy Pyridines
- Isoxazolinium Salts in Asymmetric Synthesis. 1. Stereoselective Reduction Induced by a 3’-Alkoxy Stereocentre. A New Approach to Polyfunctionalized β-Amino Acids* [1, 2]
- Enantioselective Synthesis of Epi-Emetine Analogues: Control of the Facial Selectivity in a Three-Component Domino Knoevenagel-Hetero-Diels-Alder Reaction*
- Facile Synthesis of Novel N-Aryl-4,5,6,7-tetrahydro-benzosultams by Oxyfunctionalisation of Bicyclic Isothiazolium Salts*
- Reactivity of Tetracyclic Iminium Salts of the Benzo[f]pyrido[2,1-a]- isoindole and Azepino[2,1-a]benzo[f]isoindole Type, with a Preliminary Analysis of their Interactions with Nucleic Acids*
