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Ferrier rearrangement
About: Ferrier rearrangement is a research topic. Over the lifetime, 321 publications have been published within this topic receiving 5524 citations.
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TL;DR: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature.
Abstract: Anhydrous InCl3 has been shown to efficiently catalyze the Ferrier rearrangement by a direct allylic substitution of the hydroxyl group at C-3 position of glycals to afford the corresponding 2,3-unsaturated glycosides in high yields at ambient temperature. This methodology obviates the need for protecting and/or activating the C-3 hydroxyl group of glycals. The reaction works in equal ease with both 4,6-di-O-benzyl- d -glucal and 4,6-di-O-benzyl- d -galactal. The mildness of InCl3 makes this approach compatible for glycosyl acceptors with acid labile groups. The generality of the reaction has been demonstrated with a diversity of alcohols, phenols, and sugar nucleophiles.
TL;DR: In this article, the treatment of tri-O acetyl-D-galactal with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl 2,3-unsaturated glycopyranosides 3-18 (50-86%).
Abstract: Treatment of tri-O acetyl-D-galactal 1 and tri-O-acetyl-D-glucal 2 with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl 2,3-unsaturated glycopyranosides 3-18 (50-86%).
TL;DR: In this paper, a Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor.
Abstract: A Ferrier rearrangement and β-hydroxyketone transposition are key steps in a route to a pancratistatin C-ring precursor. A key feature of the strategy is the pseudoinversion accomplished by β-hydroxyketone transposition, which allows convenient access from methyl α- d -glucopyranoside. Arylations of the C-ring by intramolecular reductive or non-reductive Pd-catalyzed conjugate addition have been demonstrated, utilizing the C1 hydroxyl to deliver the tethered aryl synthon.
TL;DR: In this paper, 2,5- cis substituted tetrahydro-and dihydro-2 H -pyranyl nucleosides have been synthesized following a stereocontrolled approach.
Abstract: Phosphonate derivatives of 2,5- cis substituted tetrahydro- and dihydro-2 H -pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4- trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5- cis -dihydro-2 H -pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5- cis -dihydro-2 H -pyranyl nucleosides.