Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
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.
Journal ArticleDOI
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.
Journal ArticleDOI
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
In vitro antitumor activity of N-glycosyl sulfonamides.
TL;DR: A series of α-D-hex-2-enopyranosyl sulfonamides was evaluated for their antiproliferative activity against human hepatocellular liver carcinoma (HepG2) and human lung adenocarcinoma (A549) cell lines.
Journal ArticleDOI
ZnCl2-catalyzed Ferrier reaction; synthesis of 2,3-unsaturated 1-O-glucopyranosides of allylic, benzylic and tertiary alcohols
B. K. Bettadaiah,P. Srinivas +1 more
TL;DR: In this article, the 3,4,6-tri-tri O -acetyl-d -glucal in dichloromethane at 25°C in the presence of ZnCl 2 was obtained in 65-91% yields, with selective formation of the α-anomer.
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n-Pentenyl esters facilitate an oxidative alternative to the Ferrier rearrangement. An expeditious route to sucrose
TL;DR: Ferrier-type reactions can now be carried out under non-acidic conditions by treating 3-n-pentenoyl glycals with iodonium dicollidinium perchlorate to afford 2,3-unsaturated disaccharides in fairly good yields.
Journal ArticleDOI
De novo asymmetric synthesis of homoadenosine via a palladium-catalyzed N-glycosylation.
TL;DR: A highly stereoselective synthesis of l-2-deoxy-beta-ribo-hexopyranosyl nucleosides from 6-chloropurine and Boc-protected pyranone has been developed using a palladium-catalyzed N-glycosylation, diastereoselectives reduction, and reductive 1,3-transposition.
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Unsaturated carbohydrates. Part VII. The preference shown by allylic ester groupings on pyranoid rings for the quasi-axial orientation
R. J. Ferrier,G. H. Sankey +1 more
TL;DR: In this paper, the proportions of anomeric 2,3-didehydro-3-deoxyaldose esters present in equilibrium mixtures, together with their conformations as revealed by n.m. spectroscopy, leads to the conclusion that in pyranoid compounds containing an endocyclic double bond allylic esters groupings, the preference is found to be 0·8 and 1·3 kcal/mole for the acetoxy- and benzoyloxy-groups, respectively.
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Stereoselective palladium-catalyzed O-glycosylation using glycals
Hahn Kim,Hongbin Men,Chulbom Lee +2 more