Topic
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: The total synthesis of (-)-kendomycin was achieved in 21 steps exploiting an effective Petasis-Ferrier union/rearrangement tactic to construct the tetrahydropyran ring, a ring-closing metathesis to generate the macrocycle, and a biomimetic quinone-methide-lactol assembly.
Abstract: The total synthesis of (−)-kendomycin (1), a novel macrocyclic polyketide with antibacterial and antitumor activity, was achieved in 21 steps (longest linear sequence) exploiting an effective Petasis−Ferrier union/rearrangement tactic to construct the tetrahydropyran ring, a ring-closing metathesis to generate the macrocycle, and a biomimetic quinone−methide−lactol assembly.
60 citations
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TL;DR: In this paper, axial anomeric sulfoxides generated via thiophenol Ferrier rearrangement of glucal and galactal derivatives are used to synthesize glycals of the gulal and allal series.
Abstract: Axial anomeric sulfoxides generated via thiophenol Ferrier rearrangement of glucal and galactal derivatives are used to synthesize glycals of the gulal and allal series. An application of the method led to the synthesis of the esperamicin thiosugar, thereby establishing its absolute configuration
58 citations
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TL;DR: The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran.
58 citations
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TL;DR: In this article, a novel and stereocontrolled glycosidation of 3,4,6-tri-O-acetyl-d-glucal with various alcohols to give the corresponding 2,3-unsaturated glycopyranosides using [bmim]Cl-1.5FeCl3 based ionic liquid is presented.
Abstract: A novel and stereocontrolled glycosidation of 3,4,6-tri-O-acetyl-d-glucal with various alcohols to give the corresponding 2,3-unsaturated glycopyranosides using [bmim]Cl–1.5FeCl3 based ionic liquid is presented. This ionic liquid has proved to be an efficient reaction medium, playing a dual role of a catalyst as well as of a solvent. Salient features of this simple methodology include non-hazardous reaction conditions, good yields in short reaction times and high anomeric selectivity.
58 citations
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TL;DR: In this article, the reaction of tri-O-acetyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.
Abstract: The reaction of tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.
58 citations