Synthesis of Hydroquinoid <i>C</i>‐ and <i>O</i>‐Biphenyl Disaccharides by Chromium‐Templated Benzannulation Reactions

Janes, Erik; Nieger, Martin; Saarenketo, Pauli; Dötz, Karl Heinz

doi:10.1002/ejoc.200300083

Cited by 14 publications

(2 citation statements)

References 92 publications

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“…194 Spirocyclic C-ribosyl arenes were also obtained by using this synthetic methodology. 197 (C-Glycosyl-aryl)-O-glycosides 164 were prepared by benzannulation of C-glycosyl acetylene 163 and O-glycosidic chromium vinylcarbene complexes 198 (Scheme 29).…”

Section: Cycloaddition Reactions To Form Aglycons Of C-glycosyl Arenesmentioning

confidence: 99%

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C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

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This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes. A classification of the preparative routes to these synthetic targets according to methodologies and compound categories is provided. Several of these compounds, regardless of their natural or synthetic origin, display antidiabetic properties due to enzyme inhibition (glycogen phosphorylase, protein tyrosine phosphatase 1B) or by inhibiting renal sodium-dependent glucose cotransporter 2 (SGLT2). The latter class of synthetic inhibitors, very recently approved as antihyperglycemic drugs, opens new perspectives in the pharmacological treatment of type 2 diabetes. Various compounds with the C-glycopyranosyl (het)arene motif were subjected to biological studies displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.

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Section: Cycloaddition Reactions To Form Aglycons Of C-glycosyl Arenesmentioning

confidence: 99%

“…( C -Glycosyl-aryl)- O -glycosides 164 were prepared by benzannulation of C -glycosyl acetylene 163 and O -glycosidic chromium vinylcarbene complexes (Scheme ).…”

Section: Synthesis Of C-glycosylation Of Arenesmentioning

confidence: 99%

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

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The Synthesis of Phenols and Quinones viaFischer Carbene Complexes

Waters

Wulff

2008

Organic Reactions

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Fischer carbene complexes can be broadly defined as those transition‐metal carbene complexes that have a low oxidation state, have an electrophilic carbene carbon , and usually have a heteroatom‐stabilizing substituent on the carbene carbon. Fischer complexes were the first examples of any type of transition metal carbene complexes to be reported. The reaction of Fischer carbene complexes with alkynes is facile, occurring just above ambient temperature, and resulting in the assembly of a benzene ring from the three carbons of the alpha, beta‐unsaturated carbine complex, the two carbons of the alkyne, and the carbon of a carbon monoxide ligand. The synthetic value of this reaction stems from its broad scope, the generally high yields for the process, and the fact that that the products can function as intermediates for the synthesis of a variety of aromatic compounds including para ‐quinones. It is the most synthetically valuable of the large number of Fischer carbene complexes that have been developed for applications in synthetic organic chemistry. This chapter is the first comprehensive review that is limited to the synthesis of phenols and quinones from the reactions of Fischer carbene complexes with alkynes.

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Utilization of Transition‐Metal Carbenoids

Herndon

2013

Transition‐Metal‐Mediated Aromatic Ring Construction

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Synthesis of Hydroquinoid C‐ and O‐Biphenyl Disaccharides by Chromium‐Templated Benzannulation Reactions

Cited by 14 publications

References 92 publications

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

The Synthesis of Phenols and Quinones viaFischer Carbene Complexes

Utilization of Transition‐Metal Carbenoids

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