Construction of quaternary stereocentres on carbohydrate scaffolds

Bera, Smritilekha; Chatterjee, Bhaskar; Mondal, Dhananjoy

doi:10.1039/c6ra13898e

Cited by 25 publications

(18 citation statements)

References 169 publications

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“…Bacterial monosaccharides can feature diversely substituted amino groups, deoxy centers, carbonyl groups, and tetrasubstituted tertiary carbon atoms at various positions on the carbohydrate ring. Tertiary‐ C sugars can be found in various natural products, having attractive biological properties [7–10] . Often these tertiary C‐atoms are substituted with a small alkyl group, commonly a methyl substituent, but more complex architectures in which functionalized alkyl chains are attached can be found as well.…”

Section: Introductionmentioning

confidence: 99%

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

et al. 2020

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The assembly of complex bacterial glycans presenting rare structural motifs and cis‐glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions in which they partake. We here report a strategy to map the reactivity of carbohydrate building blocks and apply it to understand the reactivity of the bacterial sugar, caryophyllose, a rare C12‐monosaccharide, containing a characteristic tetrasubstituted stereocenter. We mapped reactivity–stereoselectivity relationships for caryophyllose donor and acceptor glycosides by a systematic series of glycosylations in combination with the detection and characterization of different reactive intermediates using experimental and computational techniques. The insights garnered from these studies enabled the rational design of building blocks with the required properties to assemble mycobacterial lipooligosaccharide fragments of M. marinum.

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Section: Introductionmentioning

confidence: 99%

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

et al. 2020

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“…Alkene‐azide cycloaddition reaction combined with allylic azide rearrangement provides a new strategy for the preparation of imino sugars with quaternary centers . Such imino sugars have been under explored to date in drug discovery, with potential in areas such as the development of new antiviral agents based on inhibition of glycosidases.…”

Section: Discussionmentioning

confidence: 99%

A Route to 1‐Deoxynojirimycin and 1‐Deoxymannojirimycin Derivatives with Quaternary Centers Adjacent to the Ring Nitrogen from Methyl α‐d‐Mannopyranoside

Chadda

Murphy

2020

Eur J Org Chem

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6-Alkylated-8-azido-1,6-octadiene derivatives were prepared from methyl α-D-mannopyranoside. The sequence to allylic azide precursors included a Horner-Wadsworth-Emmons reaction with a concomitant epimerization that ultimately enabled synthesis of 1-deoxynojirimycin as well as 1-deoxymannojirimycin derivatives. Thermally promoted allylic acid rearrangement followed by triazoline formation, then decomposition to [a]

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“…[5][6][7][8] Several review articles on stereoselective construction of quaternary stereocenters have been nicely summarized by Brian Stoltz, and other groups. [9][10][11][12][13][14] Despite their importance and noteworthy progress in synthetic methods, the assembly of quaternary stereocenters efficiently, especially in a catalytic asymmetric manner, is still highly desired yet challenging. [15][16][17] Figure 1 Bioactive compounds containing quaternary stereocenters and their general synthetic strategies.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Zhang

Liu

et al. 2021

Synthesis

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Palladium catalyzed decarboxylative asymmetric allylic alkylation (DAAA) provides an efficient and powerful strategy to construct quaternary stereocenters which are widely present in biologically active natural products and approved drugs. In this short review, we summarize recent developments (since 2018) in the facile synthesis of quaternary stereocenters via DAAA methods. Several representative examples by using DAAA strategy for total synthesis of complex natural products further demonstrate its synthetic potential in the realm of organic and medicinal chemistry

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Construction of quaternary stereocentres on carbohydrate scaffolds

Abstract: This review describes a glimpse of the various strategies for constructing stereo-defined quaternary centres in densely functionalised carbohydrates moiety of structurally intriguing and biologically potent natural products and building blocks.

Cited by 25 publications

References 169 publications

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

A Route to 1‐Deoxynojirimycin and 1‐Deoxymannojirimycin Derivatives with Quaternary Centers Adjacent to the Ring Nitrogen from Methyl α‐d‐Mannopyranoside

Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

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