Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate

Ateş, Ali; Gautier, Arnaud; Leroy, B.; Plancher, Jean‐Marc; Quesnel, Yannick; Vanherck, Jean‐Christophe; Markó, István E.

doi:10.1016/j.tet.2003.03.002

Cited by 72 publications

(34 citation statements)

References 58 publications

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“…Condensation of propargylic alcohol 12 and previously described iodoalkyne 13 36 provided diynol 14 , which was oxidized to diynylketone 15 using Swern conditions. Ketal hydrolysis in the presence of catalytic quantities of cerium(IV) ammonium nitrate (CAN) at 70 °C gave diynone 8 in good yield 42. In addition, enol acetate formation from unsaturated ketone 15 using Et 3 N, DMAP, and Ac 2 O43 provided a mixture of E / Z isomers of 16 in 88 % yield.…”

Section: Resultsmentioning

confidence: 99%

A DNA Methyltransferase Modulator Inspired by Peyssonenyne Natural Product Structures

et al. 2012

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A novel epigenetic modulator that displays a DNMT1 inhibition and DNMT3A activation profile was characterized (compound 8). This compound is a derivative of palmitic acid that incorporates the putative reactive functional group (diynone) of the peyssonenyne natural products. Other analogues containing the diynone or an acetoxyenediyne did not show the same biological profile. In U937 human leukemia cells, diynone 8 induced cell differentiation and apoptosis, which correlated with the expression of Fas protein. Very surprisingly, diynone 8 was toxic to normal human fibroblasts (BJ) and mouse embryo fibroblasts (MEF), but not to immortalized human fibroblasts (BJEL); this unique effect was not observed with the classical DNMT inhibitor 5-azacytidine. Therefore, compound 8 interferes in a very specific manner with signaling pathways, the activities of which differ between normal and immortalized cell types. This toxicity is reminiscent of the effects of Dnmt1 ablation on mouse fibroblasts. In fact, some of the genes deregulated by the loss of Dnmt1 are similarly deregulated by 8, but not by the DNMT inhibitor SGI-1027.

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Section: Resultsmentioning

confidence: 99%

A DNA Methyltransferase Modulator Inspired by Peyssonenyne Natural Product Structures

et al. 2012

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“…Among the numerous possibilities to convert the 1,3‐dioxolan moiety to an aldehyde function,30,36,37 acid hydrolysis with strong protic acids such as trifluoroacetic acid (TFA) is the most straightforward one. However, several attempts failed including a variation of the deprotection reaction with, for example, PPTS,38 PdCl 2 ,39 DDQ40 or BiCl 3 37.…”

Section: Resultsmentioning

confidence: 99%

First Aldehyde‐Functionalized Poly(2‐oxazoline)s for Chemoselective Ligation

Taubmann

Luxenhofer

Cesana

et al. 2005

Macromolecular Bioscience

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A protected aldehyde-functionalized 2-oxazoline, 2-[3-(1,3)-dioxolan-2-ylpropyl]-2-oxazoline (DPOx), was synthesized from commercially available compounds in high yields. The polymerization of DPOx with different initiators proceeds via a living ionic mechanism; thus, the polymers were of low polydispersity and the degree of polymerization could be precisely adjusted. Copolymerization with 2-methyl-2-oxazoline gave water-soluble statistical copolymers. Hydrolysis of the homo- and copolymers resulted in well-defined, aldehyde-bearing poly(2-oxazoline)s. The aldehyde side functions reacted quantitatively with an amino-oxy compound to form the corresponding oxime.

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“…Since the general method for deprotection of ketals and acetals is acid‐mediated, this procedure is often incompatible with the presence of other sensitive functional groups in the substrate and causes partial racemization of the generated diol. We turned our attention to the recently reported method for deprotection of ketals and acetals using catalytic amounts of cerium(IV) ammonium nitrate (CAN) 19, since the mild conditions tolerate a wide range of acid‐labile functionalities and thus is appropriate to obtain MAGs with high enantiomeric excesses. The reactions were carried out at 70–80°C using an acetonitrile–water mixture (1:1) as solvent and the MAGs‐derived fatty acids were obtained in moderate to good yields.…”

Section: Methodsmentioning

confidence: 99%

Separation of regioisomers and enantiomers of underivatized saturated and unsaturated fatty acid monoacylglycerols using enantioselective HPLC

Garcia

Franco²,

Álvarez

et al. 2011

J of Separation Science

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The challenging separation of regioisomers and enantiomers of monoacylglycerols (MAGs) of fatty acids has been achieved using a single chiral HPLC column (Chiralpak® IC or Chiralpak® IA) and hexane/2-propanol eluent mixtures, without previous derivatization of the samples. The efficacy of the method is independent of the chain length and the degree of unsaturation of the fatty acids of the MAG. In addition, the separation method allows monitoring the time course for the loss of enantiomeric purity of the fatty acid-derived MAGs in polar hydroxylic solvents.

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Mild and chemoselective catalytic deprotection of ketals and acetals using cerium(IV) ammonium nitrate

Cited by 72 publications

References 58 publications

A DNA Methyltransferase Modulator Inspired by Peyssonenyne Natural Product Structures

A DNA Methyltransferase Modulator Inspired by Peyssonenyne Natural Product Structures

First Aldehyde‐Functionalized Poly(2‐oxazoline)s for Chemoselective Ligation

Separation of regioisomers and enantiomers of underivatized saturated and unsaturated fatty acid monoacylglycerols using enantioselective HPLC

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