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: Glycosidation of various glycals with furanic alcohols in presence of catalytic amount of ceric(IV) ammonium nitrate under neutral condition or using Lewis acid-catalysed proceeds smoothly to afford the corresponding 2,3-unsaturated glycosides in good yields as discussed by the authors.
Abstract: Glycosidation of various glycals with furanic alcohols in presence of catalytic amount of ceric(IV) ammonium nitrate under neutral condition or using Lewis acid-catalysed proceeds smoothly to afford the corresponding 2,3-unsaturated glycosides in good yields. In the hexose series predominantly α-D-anomers resulted while β-D-anomers are predominant in the pentose serie.
6 citations
6 citations
TL;DR: In this paper, the synthesis of carotenoid glucosides and deoxyglucosides using the acetimidate method and the Ferrier rearrangement, respectively, was described.
6 citations
TL;DR: One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis and has been extended to the synthesis of a small library of chromanone 3-C-glycosides.
5 citations
TL;DR: Two new derivatives of erythromycin have been synthesized by using glycosylation with glycal (Ferrier rearrangement), bromomethoxylation and bis(tributyltin) oxide-bromine oxidation as the key steps.
Abstract: Two new derivatives, 3''-epi-erythromycin A (2) and (9S)-11-dehydroxy-9-deoxo-9-hydroxy-11-oxoerythromycin A (3), have been synthesized by using glycosylation with glycal (Ferrier rearrangement), bromomethoxylation and bis(tributyltin) oxide-bromine oxidation as the key steps. Their antimicrobial activities were compared with those of erythromycin A (1).
5 citations