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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: A Ferrier rearrangement strategy starting from α-d-glucose gave a protected inositol, which after coupling to a chiral diacylglycerol phosphoramidite, provided a tritium-labeled, benzophenone-containing derivative of P-l-(O-aminopropyl) linked dipalmitoyl PtdIns(3,4)P2.
Abstract: A Ferrier rearrangement strategy starting from α-d-glucose gave a protected inositol, which after coupling to a chiral diacylglycerol phosphoramidite, provided a tritium-labeled, benzophenone-containing derivative of P-l-(O-aminopropyl) linked dipalmitoyl PtdIns(3,4)P2.
TL;DR: In this paper, the synthesis of the δ-lactonic fragment of pironetin (1), a natural product with outstanding antimitotic properties, was reported, achieved from commercially available tri-O-acetyl-D-glucal (6) that was employed as starting material for the preparation of ethyl ketone 4, through a synthetic sequence that included a Ferrier rearrangement of 6 and suitable functional group manipulations of the resulting O−glycoside 7 to obtain the 4−ethyl glycoside 11, together with a series
Abstract: The synthesis of the δ‐lactonic fragment of pironetin (1), a natural product with outstanding antimitotic properties, is reported. The synthesis was achieved from commercially available tri‐O‐acetyl‐D‐glucal (6) that was employed as starting material for the preparation of ethyl ketone 4, through a synthetic sequence that included a Ferrier rearrangement of 6 and suitable functional group manipulations of the resulting O‐glycoside 7 to obtain the 4‐ethyl glycoside 11, together with a series of 4‐C‐alkyl modified derivatives. The completion of the synthesis of 4 was performed via chain elongation at C‐6 by the introduction of a nitrile group and subsequent reduction, nucleophilic attack with ethyl magnesium bromide, and, finally, oxidation of the resulting alcohol 20.
TL;DR: The Ferrier rearrangement is performed with glucal (I) and a variety of structurally different alcohols as mentioned in this paper, and it is performed in the Ferrier re-arrangement.
Abstract: The Ferrier rearrangement is performed with glucal (I) and a variety of structurally different alcohols.
TL;DR: A two-step, one-pot synthetic method that relies on gold(I)-catalyzed tandem heterocyclization/Petasis-Ferrier rearrangement and Bronsted acid-assisted debenzoxylation of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes to prepare (Z)-1,2-dihydro-1tosylbenzo[b]azepin-3-ones efficiently is reported in this article.
Abstract: A two-step, one-pot synthetic method that relies on gold(I)-catalyzed tandem heterocyclization/Petasis–Ferrier rearrangement and Bronsted acid-assisted debenzoxylation of 2-(N-(prop-2-ynyl)-N-tosylamino)benzaldehydes to prepare (Z)-1,2-dihydro-1-tosylbenzo[b]azepin-3-ones efficiently is reported. The reactions proceed rapidly under mild and operationally straightforward conditions for a wide variety of aldehyde substrates containing electron-withdrawing, electron-donating, and sterically demanding functional groups and afforded the corresponding benzo-fused azaheterocyclic products in moderate to excellent yields.