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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: In this article, the Ferrier rearrangement of a methyl α-d -mannopyranoside derivative (8a), followed by a stereoselective reduction gave a l -chiro-inositol derivative (2), which was converted to l -myo- inositol 1,2,3-trisphosphate (3) and l -chirosin-inotransformer 1, 2,3,5-tetrakisphophosphate(4).
14 citations
TL;DR: An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl3(OTf) as the catalyst as discussed by the authors.
14 citations
TL;DR: A rapid and facile access to orthogonally protected 2-deoxystreptamine (2-DOS), a meso-diaminocyclitol known to be a pivotal component of most active aminoglycosides, is described here.
Abstract: The development of new aminoglycoside analogues to reduce the emergence of bacterial resistance has become a topic of high interest We describe here a rapid and facile access to orthogonally protected 2-deoxystreptamine (2-DOS), a meso-diaminocyclitol known to be a pivotal component of most active aminoglycosides Our synthetic approach started from highly protected methyl α-D-glucopyranoside which in turn was converted by a Ferrier rearrangement into an enantiopure polyfunctionalized cyclohexane ring Finally, two different N-protected groups were successively introduced The first one was inserted as an oximino benzylether followed by a diastereofacial hydride reduction, working with Me4NBH(OAc)3 only in TFA at low temperature rather than in AcOH as usual The second group was introduced by displacement of a hydroxyl group through a Mitsunobu reaction using a DPPA–DIAD–Ph3P system for azide transfer
14 citations
TL;DR: This approach provides a wide range of β-keto-functionalized 2,3-unsaturated C-glycosides in moderate to good yields and good selectivities are mainly observed with the use of D-galactal along with bulkier β- keto acids bearing phenyl moieties.
Abstract: An efficient iron-catalyzed decarboxylative C-glycosylation of glycals with β-keto acids via decarboxylative Ferrier rearrangement reaction has been established. This approach provides a wide range of β-keto-functionalized 2,3-unsaturated C-glycosides in moderate to good yields. Good selectivities are mainly observed with the use of D-galactal along with bulkier β-keto acids bearing phenyl moieties.
14 citations
TL;DR: Suitably protected carbocyclic pseudo-sugars were synthesised from d -glucosamine via a Ferrier rearrangement as discussed by the authors. But their precursors were derived from β-1,4-pseudo-disaccharides related to the chitinase inhibitor, allosamidin.
13 citations