Topic
Ferrier carbocyclization
About: Ferrier carbocyclization is a research topic. Over the lifetime, 66 publications have been published within this topic receiving 947 citations.
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TL;DR: In this paper, a 1,3- or 1,5-rearrangement of N,O-acetals in dichloromethane was described, and crossover experiments indicated that the reaction proceeded through an ion pair intermediate.
8 citations
TL;DR: In this paper, an efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from Nacetylglucosamine is described.
7 citations
TL;DR: The application of the Ferrier carbocyclization reaction to the synthesis of enantiopure InoAz analogues starting from readily available azido glucosides is investigated and is expected to facilitate continued development of synthetic Ino Az analogues as inhibitors or MCRs of inositol-containing glycoconjugates in eukaryotic and mycobacterial systems.
Abstract: Azide-modified inositol (InoAz) analogues are valuable as inhibitors and have shown promise as metabolic chemical reporters (MCRs) for labeling inositol-containing glycoconjugates in eukaryotic cells and potentially in mycobacteria, but the synthesis of enantiomerically pure InoAz analogues via traditional approaches is challenging. As a complementary route, here we investigated the application of the Ferrier carbocyclization reaction to the synthesis of enantiopure InoAz analogues starting from readily available azido glucosides. Using this approach combined with a para-methoxybenzyl protecting group strategy, 3-azido-3-deoxy- and 4-azido-4-deoxy-d-myo-inositol were efficiently synthesized. 5-Azido-5-deoxy-d-myo-inositol was inaccessible due to an unusual β-elimination reaction, wherein the azide anion acted as the leaving group. The reported strategy is expected to facilitate continued development of synthetic InoAz analogues as inhibitors or MCRs of inositol-containing glycoconjugates in eukaryotic and mycobacterial systems.
7 citations
TL;DR: Amino acid 2,3-unsaturated glycopyranosyls have been prepared by the Ferrier rearrangement of acetyl protected glucals and PEG-bound amino acids in the presence of a catalytic quantity of BF3·Et2O in CH2Cl2 at ambient temperature.
7 citations
TL;DR: In this article, the reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(lV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.
Abstract: The reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(lV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.
6 citations