Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
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TLDR
A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.About:
This article is published in European Journal of Organic Chemistry.The article was published on 2013-11-01. It has received 121 citations till now. The article focuses on the topics: Ferrier rearrangement & Ferrier carbocyclization.read more
Citations
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Journal ArticleDOI
Methods for 2-Deoxyglycoside Synthesis.
Clay S. Bennett,M. Carmen Galan +1 more
TL;DR: This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter.
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Recent progress of C-glycosylation methods in the total synthesis of natural products and pharmaceuticals
TL;DR: This review highlights the C-glycosylation methods that have been practised in the total synthesis of natural products and pharmaceuticals in the past decade.
Journal ArticleDOI
Recent developments in β-C-glycosides: synthesis and applications
Krishnamoorthy Lalitha,Kumarasamy Muthusamy,Y. Siva Prasad,Praveen Kumar Vemula,Subbiah Nagarajan +4 more
TL;DR: In the last few years, considerable progress has been made in the synthesis of C-glycosides as mentioned in this paper, and due to its versatility, C glycosides play a pivotal role in developing novel materials, surfactants and bioactive molecules.
Journal ArticleDOI
Stereoelectronic power of oxygen in control of chemical reactivity: the anomeric effect is not alone
Igor V. Alabugin,Leah Kuhn,Michael G. Medvedev,Michael G. Medvedev,Nikolai V. Krivoshchapov,Nikolai V. Krivoshchapov,Vera A. Vil,Ivan A. Yaremenko,Patricia Mehaffy,Meysam Yarie,Alexander O. Terent'ev,Mohammad Ali Zolfigol +11 more
TL;DR: In this article, the authors evaluate the fundamental connections between the anomeric effect and a broad variety of O-functional groups and highlight the vast implications of AE for the structure and reactivity of organic O-functionalities.
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Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis
TL;DR: This review summarizes the literature on the different transformations of the endo glycals into biologically relevant compounds as well as on the use of glycals as chiral building blocks for the synthesis of various natural products such as aspicilin, reblastatin, diospongins, decytospolides, osmundalactones, paclitaxel, isatisine, d-fagomine, and spliceostatin, reported post 2014.
References
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Journal ArticleDOI
Trifluoroacetic acid-mediated facile transformation of 2-C-hydroxymethyl-D-glycals to chiral pyrano[2,3-b]benzopyrans.
TL;DR: Treatment of 2-C-hydroxymethyl-D-glycals with phenols in trifluoroacetic acid at ambient temperature leads to an extremely facile transformation affording chiral pyrano[2,3-b]benzopyrans in high yields.
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Unsaturated carbohydrates. Part XV. The synthesis of (3′-deoxyhex-2′-enopyranosyl)purine derivatives
R. J. Ferrier,M. M. Ponpipom +1 more
TL;DR: Fusion of 3-deoxyhex-2-enopyranosyl esters or the isomeric 2-hydroxy glycal esters with theophylline or 2,6-dichloropurine in the presence of an acidic catalyst affords (3′-Deoxyhex, 2′-ENopyranoyl)purine nucleoside derivatives as mentioned in this paper.
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Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors
TL;DR: In this article, it was shown that the peptide precursors derived from serine can be coupled to a sugar derivative by an indium mediated alkynylation reaction.
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Environmentally Benign Synthesis of 2,3-Unsaturated Glycopyranosides in Task-Specific Ionic Liquid
Goutam Guchhait,Anup Kumar Misra +1 more
TL;DR: A green reaction condition has been developed for the synthesis of 2,3-unsaturated glycopyranosides by the Ferrier rearrangement of glycals using alcohols and thiols in 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([BMIM]·OTf) in excellent yield as mentioned in this paper.
Journal ArticleDOI
Synthesis of 2,3-unsaturated furanic hex- and pent-enopyranoside employing the ferrier rearrangement
TL;DR: Glycosidation of various glycals with furanic alcohols in presence of catalytic amount of ceric(IV) ammonium nitrate under neutral condition or using Lewis acid-catalysed proceeds smoothly to afford the corresponding 2,3-unsaturated glycosides in good yields as discussed by the authors.
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