Iminosugar <i>C</i>-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars

Prasad, Sure Siva; Senthilkumar, Soundararasu; Srivastav, Ajeet K.; Baskaran, Sundarababu

doi:10.1021/acs.orglett.7b02175

Cited by 32 publications

(6 citation statements)

References 45 publications

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“…Our sustained interest toward the synthesis of biologically significant iminosugars has recently resulted in the development of a novel and facile one-pot strategy for the stereoselective synthesis of novel iminosugar C -nitromethyl glycosides and subsequent single-step transformations to structurally unique bicyclic iminosugars (Scheme ). Though the 1,3-dipolar cycloaddition of nitrone has been extensively applied in the synthesis of iminosugars, the intramolecular nitrile oxide cycloaddition (INOC) has not been explored in the synthesis of functionalized iminosugars.…”

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confidence: 99%

Iminosugar C-Nitromethyl Glycoside: Stereoselective Synthesis of Isoxazoline and Isoxazole-Fused Bicyclic Iminosugars

Prasad

Baskaran

2018

J. Org. Chem.

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A simple and efficient method for the stereoselective synthesis of isoxazoline/isoxazole-fused iminosugar derivatives has been developed using intramolecular nitrile oxide cycloaddition (INOC) as a key step. Iminosugar C-nitromethyl glycosides, derived from simple carbohydrates, served as excellent nitrile oxide precursors in 1,3-dipolar cycloaddition reactions. N-Alkenyl iminosugar C-nitromethyl glycosides afforded novel isoxazoline-fused indolizidine-, pyrrolizidine-, and quinolizidine-based iminosugars in excellent yields with a high degree of stereoselectivity, whereas N-alkynyl iminosugar C-nitromethyl glycosides furnished the corresponding isoxazole containing tricyclic iminosugars in very good yields.

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confidence: 99%

Iminosugar C-Nitromethyl Glycoside: Stereoselective Synthesis of Isoxazoline and Isoxazole-Fused Bicyclic Iminosugars

Prasad

Baskaran

2018

J. Org. Chem.

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“…[92] Similarly Baskaran and coworkers have prepared iminosugar C-nitromethyl glycosides from 167 by the action of an aliphatic amine and nitromethane. [93] The use of imidazole nitrogen as a nucleophile was employed in the synthesis of nagstatin 16. [94] The precursor 168, an l-ribofuranose derivative, was converted to sulfonate 169 in two steps (addition of lithiated imidazole derivative to the latent aldehyde of 170 and sulfonation).…”

Section: Imine or Imidazole Nitrogen As A Nucleophilementioning

confidence: 99%

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

Dhara

Bennett

Murphy

2021

The Chemical Record

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This personal account focuses on synthesis of polyhydroxylated piperidines, a subset of compounds within the iminosugar family. Cyclisations to form the piperidine ring include reductive amination, substitution via amines, iminium ions and cyclic nitrones, transamidification (N-acyl transfer), addition to alkenes, ring contraction and expansion, photoinduced electron transfer, multicomponent Ugi reaction and ring closing metathesis. Enantiomerically pure piperidines are obtained from chiral pool precursors (e. g. sugars, amino acids, Garner's aldehyde) or asymmetric reactions (e. g. epoxidation, dihydroxylation, aminohydroxylation, aldol, biotransformation). Our laboratory have contributed cascades based on reductive amination from glycosyl azide precursors as well as Huisgen azide-alkene cycloaddition. The latter's combination with allylic azide rearrangement has given substituted piperidines, including those with quaternary centres adjacent to nitrogen.

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“…In 2017, Baskaran and coworkers reported the development of novel methods for the synthesis of iminosugar C-nitromethyl glycosides and bicyclic iminosugars (Prasad et al, 2017). The first group of compounds could be obtained from D-ribose tosylate 57, by treatment with an amine at room temperature, and subsequent alkylation of the iminium ion generated in situ with nitromethane (Figure 4C).…”

Section: Imino Sugars and Other Carbohydrate Derivativesmentioning

confidence: 99%

The Stereoselective Nitro-Mannich Reaction in the Synthesis of Active Pharmaceutical Ingredients and Other Biologically Active Compounds

2020

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The nitro-Mannich (aza-Henry) reaction, in which a nitroalkane and an imine react to form a β-nitroamine, is a versatile tool for target-oriented synthesis. Although the first stereoselective reaction was developed only 20 years ago, and enantioselective and diastereoselective versions for the synthesis of non-racemic compounds soon after, there are nowadays a variety of reliable methods which can be used for the synthesis of APIs and other biologically active substances. Hence many anticancer drugs, antivirals, antimicrobials, enzyme inhibitors and many more substances, containing C-N bonds, have been synthesized using this reaction. Several transition metal complexes and organocatalysts were shown to be compatible with the presence of a wide range of functional groups in these molecules, and very high levels of asymmetric induction have been achieved in some cases. The reaction has also been applied in cascade processes. The structural diversity of the products, ranging from simple heterocycles or azabicycles to complex alkaloids, iminosugars, amino acids or diamino acids and phosphonates, shows the versatility of the nitro-Mannich reaction and its potential for future developments.

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Iminosugar C-Nitromethyl Glycosides and Divergent Synthesis of Bicyclic Iminosugars

Cited by 32 publications

References 45 publications

Iminosugar C-Nitromethyl Glycoside: Stereoselective Synthesis of Isoxazoline and Isoxazole-Fused Bicyclic Iminosugars

Iminosugar C-Nitromethyl Glycoside: Stereoselective Synthesis of Isoxazoline and Isoxazole-Fused Bicyclic Iminosugars

Cyclisations and Strategies for Stereoselective Synthesis of Piperidine Iminosugars

The Stereoselective Nitro-Mannich Reaction in the Synthesis of Active Pharmaceutical Ingredients and Other Biologically Active Compounds

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