Synthesis of furan derivatives of cyclic β-amino acid cispentacin via intramolecular nitrile oxide cycloaddition

Basak, Ranjan Kumar; Suresh, D.; Vankar, Yashwànt D.

doi:10.1016/j.tetlet.2012.05.126

Cited by 7 publications

(3 citation statements)

References 47 publications

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“…634 was next oxidized to β-amino ester derivative 635 . Ketal hydrolysis and diol oxidative cleavage finally afforded tetrahydrofuran amino ester 637 (Scheme ) …”

Section: Cyclic β-Amino Acids With a Heteroatom In The Ringmentioning

confidence: 99%

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Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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Introduction 1116 2. Carbocyclic β-Amino Acids 1118 2.1. Syntheses of Five-or Six-Membered Carbocyclic β-Amino Acids 1118 2.1.1. Carbocyclic β-Amino Acids from β-Keto Esters 1119 2.1.2. Carbocyclic β-Amino Acids by Metathesis 1119 2.1.3. Carbocyclic β-Amino Acids by Amino Group Conjugate Addition 1122 2.1.4. Carbocyclic β-Amino Acids by Cycloaddition 1124 2.1.5. Carbocyclic β-Amino Acids by Desymmetrization of meso-Anhydrides 1124 2.1.6. Carbocyclic β-Amino Acids from Natural Sources 1125 2.1.7. Miscellaneous 1127 2.2. Syntheses of Small-Ring Carbocyclic β-Amino Acids 1128 2.3. Syntheses of Carbocyclic β-Amino Acids with Larger Ring Systems 1129 2.4. Synthesis of Functionalized Carbocyclic β-Amino Acids 1131 2.4.1. Syntheses of Functionalized Cyclic β-Amino Acids by C−C Double Bond Functionalization 1131 2.4.2. Several Relevant Routes to Functionalized Cyclic β-Amino Acids Other Than Functionalization of the Ring C−C Double Bond 1137 3. Cyclic β-Amino Acids with a Heteroatom in the Ring 1137 3.1. Syntheses of Cyclic β-Amino Acids with a N Atom in the Ring 1138 3.1.1. Three-and Four-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.2. Five-Membered N-Containing Cyclic β-Amino Acids 1138 3.1.3. Six-Membered N-Containing Cyclic β-Amino Acids 1145 3.1.4. N-Containing Cyclic β-Amino Acids with Larger Ring Systems 1148 3.2. Syntheses of Cyclic β-Amino Acids with an O Atom in the Ring 1148 3.2.1. Four-Membered O-Containing Cyclic β-Amino Acids 1148 3.2.2. Five-Membered O-Containing Cyclic β-Amino Acids 1149 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids 1155 3.3. Cyclic β-Amino Acids with Other Heteroatoms in the Ring 1159 4. Some Relevant Biological Properties of Cyclic β-Amino Acids 1160 4.1. Cyclic β-Amino Acids Possessing Antifungal or Antibacterial Properties 1160 4.2. Antiviral Cyclic β-Amino Acids 1162 4.3. Cyclic β-Amino Acids with Antitumoral Properties 1162 4.4. Cyclic β-Amino Acids with Cardioprotective

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“…634 was next oxidized to β-amino ester derivative 635 . Ketal hydrolysis and diol oxidative cleavage finally afforded tetrahydrofuran amino ester 637 (Scheme ) …”

Section: Cyclic β-Amino Acids With a Heteroatom In The Ringmentioning

confidence: 99%

“…Ketal hydrolysis and diol oxidative cleavage finally afforded tetrahydrofuran amino ester 637 (Scheme 128). 154 3.2.3. Six-Membered O-Containing Cyclic β-Amino Acids.…”

Section: Syntheses Of Cyclic β-Amino Acids With An O Atom In the Ringmentioning

confidence: 99%

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

2013

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“…The reaction mixture was allowed to reach room temperature (RT) and stirred for 21 h. The excess nitromethane was removed under reduced pressure. The crude mixture is then purified by column chromatography on silica gel (hexane/EtOAc = 3/7 as eluent, KMnO 4 stained)[20]. After removing the solvents under reduced pressure, a yellow oil was obtained (2.55 g, 94%).…”

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confidence: 99%

Organocatalytic Michael Addition to (D)-Mannitol-Derived Enantiopure Nitroalkenes: A Valuable Strategy for the Synthesis of Densely Functionalized Chiral Molecules

et al. 2019

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Carbohydrates are abundant renewable resources and are a feedstock for green chemistry and sustainable synthesis of the future. Among the hexoses and the pentoses present in biomass, mannitol was selected in the present project as a valuable platform, directly available from the chiral pool, to build highly functionalized molecules. Starting from (R)-2,3-O-cyclohexylidene glyceraldehyde, which is easily prepared in a large scale from D-mannitol, an enantiopure chiral nitro alkene was prepared by reaction with nitromethane, and its reactivity studied. Organocatalytic Michael addition of dimethyl malonate, β-keto esters, and other nucleophiles on the nitro alkene afforded high stereoselectivity and densely functionalized chiral molecules, which were further synthetically developed, leading to five-membered lactones and bicyclic lactams. Preliminary studies showed that the metal-free catalytic reaction on the chiral nitro alkene can be performed under continuous flow conditions, thus enabling the use of (micro)mesofluidic systems for the preparation of enantiomerically pure organic molecules from the chiral pool.

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Diastereoselective Synthesis of Highly Substituted, Amino‐ and Pyrrolidino‐Tetrahydrofurans as Lead‐Like Molecular Scaffolds

Wales

Merişor²,

Adcock³

et al. 2018

Chemistry A European J

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A series of highly substituted tetrahydrofurans (THFs), decorated with modifiable 2-aryl, 3-carboxy and 4-amino substituents, has been prepared for biological evaluation within the European Lead Factory. Diastereoselective reductive amination of pre-functionalised 4-oxofurans, readily prepared from cinnamate esters via oxa-Michael/Dieckmann annulation, provided the requisite THF cores on gram scale with three contiguous stereocentres, including full substitution at C-3. In a second series, a pyrrolidine ring was fused to the same oxofuran scaffold via an intramolecular reductive amination, inverting the configuration at C-4 relative to the other ring substituents. The resulting compounds, which displayed desirable physical properties as lead-like scaffolds, were derivatised into a small library of 24 compounds, demonstrating their ability to serve as starting points for drug discovery. Ultimately, this chemistry enabled the preparation of 1948 THF-containing compounds for inclusion in the Joint European Compound Library.

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Synthesis of furan derivatives of cyclic β-amino acid cispentacin via intramolecular nitrile oxide cycloaddition

Cited by 7 publications

References 47 publications

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

Synthesis of Carbocyclic and Heterocyclic β-Aminocarboxylic Acids

Organocatalytic Michael Addition to (D)-Mannitol-Derived Enantiopure Nitroalkenes: A Valuable Strategy for the Synthesis of Densely Functionalized Chiral Molecules

Diastereoselective Synthesis of Highly Substituted, Amino‐ and Pyrrolidino‐Tetrahydrofurans as Lead‐Like Molecular Scaffolds

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