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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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
Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides
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Mechanisms of enzymatic CO bond cleavages in deoxyhexose biosynthesis
Xuemei He,Hung Wen Liu +1 more
TL;DR: The increasing amount of knowledge about the biosynthesis of deoxysugars may allow the assembly of a repertoire of novel sugar structures through recruitment and collaborative action of genes from a variety of biosynthetic pathways to create diverse secondary metabolites in the search for novel antibiotic/antitumour agents.
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Stereospecific glycosylation via Ferrier rearrangement for optical resolution
TL;DR: Diastereospecific glycosylation of racemic alcohols by reaction with suitable glycal derivatives in the presence of iodine provides easy access to both enantiomers as illustrated by the preparation of an optically pure α-hydroxy β-lactam that is an intermediate for the semisynthesis of taxol.
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712. The reaction between 3,4,6-tri-O-acetyl-D-glucal and p-nitrophenol
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Nucleophilic Addition of Potassium Alkynyltrifluoroborates to d-Glucal Mediated by BF3·OEt2: Highly Stereoselective Synthesis of α-C-glycosides
Adriano S. Vieira,Pedro F. Fiorante,Thomas L. S. Hough,Fernando P. Ferreira,Diogo S. Lüdtke,Hélio A. Stefani +5 more
TL;DR: A convenient, mild and highly stereoselective method for C-glycosidation (alkynylation) of D-glucal with various potassium alkynyltrifluoroborates, mediated by BF3x OEt2 and involving oxonium intermediates, preferentially provides the alpha-acetylene glycoside products with good yields.
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