Showing papers on "Ferrier rearrangement published in 2015"
TL;DR: A convergent total synthesis of 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri-O-acetyl-D-glucal 7 is reported in this paper.
Abstract: A convergent total synthesis of a 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri-O-acetyl-D-glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7, cross metathesis between chiral fragments 3 and 4, Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.
20 citations
TL;DR: In this paper, a method to prepare 3-alkoxyindanones efficiently by gold-catalyzed tandem cycloisomerization/Petasis-Ferrier rearrangement from ortho-ethynylarylaldehydes with alcohols is described.
Abstract: A method to prepare 3-alkoxyindanones efficiently by gold-catalyzed tandem cycloisomerization/Petasis–Ferrier rearrangement from ortho-ethynylarylaldehydes with alcohols is described. The reaction was accomplished in moderate to excellent yields under mild reaction conditions and also offers a convenient synthetic route to 3-alkoxycyclopentenones.
20 citations
TL;DR: The aim of this review is to highlight the rich chemistry of ∆-2,3 unsaturated pyranosides, emphasizing the variety of transformations that have been carried out in these substrates during the last decade.
Abstract: Unsaturated carbohydrate derivatives are useful intermediates in synthetic transformations leading to a variety of compounds. The aim of this review is to highlight the rich chemistry of ∆-2,3 unsaturated pyranosides, emphasizing the variety of transformations that have been carried out in these substrates during the last decade.
16 citations
TL;DR: The osmium-catalyzed aminohydroxylation of glycals has been achieved with complete regio- and stereocontrol by taking advantage of the Donohoe tethering approach.
11 citations
TL;DR: A general approach for the synthesis of carbonic anhydrases glycoinhibitors belonging to an aminoxysulfonamide series is presented using a Ferrier sulfonamidoglycosylation reaction on glycals.
Abstract: A general approach for the synthesis of carbonic anhydrases glycoinhibitors belonging to an aminoxysulfonamide series is presented using a Ferrier sulfonamidoglycosylation reaction on glycals. All the compounds showed good in vitro inhibitory activity against four human carbonic anhydrase isoforms, with selectivity against the cytosolic (hCA II) vs the tumor associated (hCA IX and XII) enzymes.
10 citations
TL;DR: In this paper, an efficient Ferrier Rearrangement reaction system using Tm(OTf) 3 as the catalyst was established, and a series of O -, S -, N -, and C -2, 3-unsaturated-glucosides were obtained in good yields and high anomeric selectivities by the glycosidation of 3,4,6-tri-O -acetyl-d -glucal with the corresponding nucleophiles, including azaglycosylation with N -nucleophiles.
8 citations
TL;DR: In this article, two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2, 3-triazoles using Ferrier rearrangement.
Abstract: Two strategies were considered for the synthesis of 2,3-unsaturated O-glucosyl-1,2,3-triazoles. The first, involving reaction between tri-O-acetyl- d -glucal and triazole alcohols gave no stereoselectivity. A second strategy provided 2,3-unsaturated O-glycosides from glycals and alkynols through a Ferrier rearrangement; this method, employing montmorillonite K-10 doped with iron(III) chloride hexahydrate in dichloromethane afforded new glycosides in good to excellent yields within short times and with high α-stereoselectivities. Subsequently, the glucosides were coupled with 2-azido-1,4-naphthoquinone to produce a new series of 1,2,3-1H-triazolyl O-glucoside derivatives through a click reaction.
7 citations
TL;DR: The same procedure proved to be appropriate in synthesizing dihydropyran derivatives ('C-glycosides') using allyltrimethylsilane as the nucleophile (only 'α-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.
7 citations
6 citations
TL;DR: α-2,3-Unsaturated galactosides were synthesized by the initial activation of d-galactals with diethyl phosphorochloridite and the subsequent glycosyl addition via Ferrier rearrangement with various O-nucleophiles in the presence of AlCl3 to give the glycoside products with excellent α-stereoselectivity.
4 citations
TL;DR: In this article, a new catalyst system AuCl3/phenylacetylene is developed to promote the Ferrier rearrangement of glycals and the O-glycosylation of 1-O-acetyl sugars.
Abstract: A new catalyst system AuCl3/phenylacetylene is developed to promote the Ferrier rearrangement of glycals and the O-glycosylation of 1-O-acetyl sugars.
TL;DR: Tm(OTf)3 is shown to be a highly efficient catalyst for the preparation of various 2,3-unsaturated glycosides in Ferrier rearrangement reactions as mentioned in this paper.
Abstract: Tm(OTf)3 is shown to be a highly efficient catalyst for the preparation of various 2,3-unsaturated glycosides in Ferrier rearrangement reactions.
TL;DR: In this article, Ferrier rearrangement of tri-O-acetyl-D-glucal in the presence of various alcohols was used to obtain 2,3-unsaturated glycosides with good α-selectivity.
Abstract: 2,3-Unsaturated glycosides (20 examples) are obtained with good α-selectivity by Ferrier rearrangement of tri-O-acetyl-D-glucal (I) in the presence of various alcohols (II).
TL;DR: In this paper, Ferrier rearrangement with tri-O-acetyl-D-glucal was applied to 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanols with baker's yeast.
Abstract: 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanones 4a-e have been reduced to optically active 4-[3-(aryl)-1,2,4-oxadiazol-5-yl] butanols 5a-e with baker's yeast. We subjected the alcohols possessing (S)-configuration to Ferrier' rearrangement with tri-O-acetyl-D-glucal 6 which furnished new unsaturated O-glycosides 7a-e. The crystallographic data of the glycosides 7b confirmed the (S)-configuration for the aglycone portion of the carbon atom.
TL;DR: A novel route to access functionalized oxepanes and 2-deoxyseptanosides through Ferrier type ring-expansion of carbohydrate based vinylcyclopropanes is developed in this paper.
Abstract: A novel route to access functionalized oxepanes and 2-deoxyseptanosides through Ferrier type ring-expansion of carbohydrate based vinylcyclopropanes is developed.
TL;DR: The first example of intermolecular regio- and stereoselective C- glycosylation of glycals with a range of easily prepared β-keto acids to form structurally diverse ketone functionalized C-glycosides with moderate to good yields is developed.
Abstract: The first example of intermolecular regio- and stereoselective C-glycosylation of glycals with a range of easily prepared β-keto acids to form structurally diverse ketone functionalized C-glycosides with moderate to good yields is developed.
TL;DR: In this paper, a new approach for the preparation of biaryl derivatives was developed by using the gold-catalyzed cycloisomerization of propargylbenzyl methyl ethers under mild reaction conditions.
Abstract: A new approach for the preparation of biaryl derivatives is developed by using the gold-catalyzed cycloisomerization of propargylbenzyl methyl ethers under mild reaction conditions.