Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

Kinfe, Henok H.

doi:10.1039/c9ob00343f

Cited by 60 publications

(34 citation statements)

References 98 publications

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“…[23] 1,2-Unsaturated sugar derivatives, the so-called glycals, have also found vast application in carbohydrate chemistry. [24] Their great versatility makes them privileged substrates for chemical diversification based on the sugar scaffold. Indeed, glycals are not only used for the synthesis of O, S, and C-glycosides but also for conducting various transformations including epoxidation, cyclopropanation, Ferrier rearrangement as well as alkene functionalization, to name a few examples.…”

Section: Glycosyl Donorsmentioning

confidence: 99%

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Glycosylation and Protecting Group Strategies Towards the Synthesis of Saponins and Bacterial Oligosaccharides: A Personal Account

Muru

Gauthier

2021

The Chemical Record

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Carbohydrates and their conjugates are not only involved in important biological processes but are also regarded as promising therapeutics and prophylactics. Over the last century, several glycosylation methodologies, glycosyl donors, and protecting groups have been developed and some of them have found broad synthetic applications in carbohydrate chemistry. In this Personal Account, we describe how glycosylation and protecting group strategies have been implemented in our as well as in other research groups as to synthesize bioactive glycans, more specifically naturally occurring lupane‐type saponins as well as oligosaccharides related to Burkholderia species.

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Section: Glycosyl Donorsmentioning

confidence: 99%

“…1,2‐Unsaturated sugar derivatives, the so‐called glycals, have also found vast application in carbohydrate chemistry [24] . Their great versatility makes them privileged substrates for chemical diversification based on the sugar scaffold.…”

Section: Introductionmentioning

confidence: 99%

Glycosylation and Protecting Group Strategies Towards the Synthesis of Saponins and Bacterial Oligosaccharides: A Personal Account

Muru

Gauthier

2021

The Chemical Record

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“…Furthermore, interest in generating novel synthetic scaffolds has recently declined in pharmaceutical research due to the elaborate isolation procedures required or lengthy total synthesis pathways [9]. Recently, there has been increased interest in NP-inspired or NP-like products to improve the chemical diversity of NPs through different routes: (1) diversity-oriented synthesis (DOS) starting from isolated NPs [10,11], (2) expansion of NP space catalysed by uncommon P450 reactions [12], (3) construction of new lead compounds inspired by bioactive NPs [13], (4) recombined NP moieties generated via coupling reactions [14], (5) diversity-enhanced extraction directly from plants [15]. In particular easily…”

Section: Introductionmentioning

confidence: 99%

Meroterpene-Like α-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from β-Caryophyllene

et al. 2020

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Background: Natural meroterpenes derived from phloroglucinols and β-caryophyllene have shown high inhibitory activity against α-glucosidase or cancer cells, however, the chemical diversity of this type of skeletons in Nature is limited. Methods: To expand the chemical space and explore their inhibitory activities against α-glucosidase (EC 3.2.1.20), we employed β-caryophyllene and some natural moieties (4-hydroxycoumarins, lawsone or syncarpic acid) to synthesize new types of meroterpene-like skeletons. All the products (including side products) were isolated and characterized by NMR, HR-MS, and ECD. Results: In total, 17 products (representing seven scaffolds) were generated through a one-pot procedure. Most products (12 compounds) showed more potential activity (IC50 < 25 μM) than the positive controls (acarbose and genistein, IC50 58.19, and 54.74 μM, respectively). Compound 7 exhibited the most potent inhibition of α-glucosidase (IC50 3.56 μM) in a mixed-type manner. The CD analysis indicated that compound 7 could bind to α-glucosidase and influence the enzyme’s secondary structure. Conclusions: Compound 7 could serve as a new type of template compound to develop α-glucosidase inhibitors. Full investigation of a biomimic reaction can be used as a concise strategy to explore diverse natural-like skeletons and search for novel lead compounds.

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“…Given their importance, many strategies have been developed for C ‐glycosylation and, among them, some of the most attractive involve the functionalization of unsaturated sugars derivatives, known as glycals . Typical approaches rely on classical cross‐coupling procedures, such as the Heck, Suzuki–Miyaura and Stille reactions …”

Section: Introductionmentioning

confidence: 99%

Carbonylative Negishi‐Type Coupling of 2‐Iodoglycals with Alkyl and Aryl Halides

et al. 2019

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Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

Abstract: Versatility of glycals in the stereoselective synthesis of natural products.

Cited by 60 publications

References 98 publications

Glycosylation and Protecting Group Strategies Towards the Synthesis of Saponins and Bacterial Oligosaccharides: A Personal Account

Glycosylation and Protecting Group Strategies Towards the Synthesis of Saponins and Bacterial Oligosaccharides: A Personal Account

Meroterpene-Like α-Glucosidase Inhibitors Based on Biomimetic Reactions Starting from β-Caryophyllene

Carbonylative Negishi‐Type Coupling of 2‐Iodoglycals with Alkyl and Aryl Halides

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