Stereoselective synthesis of CD-ring precursors of vitamin D derivatives

Rodriguez, Raphaël; Chapelon, Anne‐Sophie; Ollivier, Cyril; Santelli, Maurice

doi:10.1016/j.tet.2009.06.052

Cited by 24 publications

(12 citation statements)

References 79 publications

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“…For instance, remarkable Lewis acid-catalysed one-pot assemblies of suitable anilines and glycals have enabled the construction of the core structure of marmycin A devoid of the C7′ methyl group17,18. The presence of alkyl substituents at the junction of bicyclic systems is a ubiquitous feature of natural products, as illustrated by taxanes20 and steroids21, and represents a significant synthetic obstacle in some cases. Regardless, these pioneering studies have provided relevant clues and set important milestones towards achieving these complex structures.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of marmycin A and investigation into its cellular activity

Cañeque¹,

Gomes²,

Thi³

et al. 2015

Nature Chem

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Anthracyclines such as doxorubicin are used extensively in the treatment of cancers. Anthraquinone-related angucyclines also exhibit antiproliferative properties and have been proposed to operate via similar mechanisms, including direct genome targeting. Here, we report the chemical synthesis of marmycin A and the study of its cellular activity. The aromatic core was constructed by means of a one-pot multistep reaction comprising a regioselective Diels-Alder cycloaddition, and the complex sugar backbone was introduced through a copper-catalysed Ullmann cross-coupling, followed by a challenging Friedel-Crafts cyclization. Remarkably, fluorescence microscopy revealed that marmycin A does not target the nucleus but instead accumulates in lysosomes, thereby promoting cell death independently of genome targeting. Furthermore, a synthetic dimer of marmycin A and the lysosome-targeting agent artesunate exhibited a synergistic activity against the invasive MDA-MB-231 cancer cell line. These findings shed light on the elusive pathways through which anthraquinone derivatives act in cells, pointing towards unanticipated biological and therapeutic applications.

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Section: Resultsmentioning

confidence: 99%

Synthesis of marmycin A and investigation into its cellular activity

Cañeque¹,

Gomes²,

Thi³

et al. 2015

Nature Chem

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“…The direct determination of the concentration of the xanthate group at the surface of the nanoparticles was not possible by UV–vis spectroscopy; thus, it was estimated based on the Ellman's test protocol . This method relies on the quantification of the number of SH groups; therefore, the xanthates anchored to surface of the MNPs were transformed into sulfhydryl groups in reaction with ethylenediamine (ethanol, 4 h, room temperature (r.t.)) . The number of SH groups calculated by Ellman's method is 0.02 mmol g −1 .…”

Section: Resultsmentioning

confidence: 99%

“…[ 15 ] This method relies on the quantifi cation of the number of SH groups; therefore, the xanthates anchored to surface of the MNPs were transformed into sulfhydryl groups in reaction with ethylenediamine (ethanol, 4 h, room temperature (r.t.)). [ 16 ] The number of SH groups calculated by Ellman's method is 0.02 mmol g −1 .…”

Section: Macromolecularmentioning

confidence: 99%

Surface‐Initiated RAFT/MADIX Polymerization on Xanthate‐Coated Iron Oxide Nanoparticles

Wilczewska

Markiewicz

2013

Macro Chemistry & Physics

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A new strategy for the preparation of magnetite/silica/(co)polymer core/shell nanoparticles is described. The reversible addition‐fragmentation chain transfer/macromolecular design via interchange of xanthates (RAFT/MADIX) polymerization agent — xanthate/dithiocarbonate — is covalently anchored to the aminosilica‐coated iron oxide nanoparticles surface by its R‐group. Subsequently, polymerization and copolymerization of vinyl monomers on such synthesized structures are carried out. Fourier transform infrared (FTIR) spectroscopy, UV–vis spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), X‐ray diffraction (XRD), energy‐dispersive X‐ray (EDX) analysis, and transmission electron microscopy (TEM) are employed to confirm the grafting and study the chemical composition of the obtained structures.

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“…4 Nevertheless, when a noncommercial or more complex -functionalized methyl ketone is required, sometimes its synthesis is far from trivial. Another strategy to access xanthylmethyl ketones is by the reaction of lithium enolates of methyl ketones with bisxanthate, 14 however, this method requires the use of a strong base which limits the functional group tolerance. Therefore, alternative methods for the synthesis of these valuable building blocks from readily available materials are desirable.…”

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confidence: 99%

α-Xanthylmethyl Ketones from α-Diazo ketones

Miranda¹,

López‐Mendoza²

2021

Synthesis

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A simple and efficient method to obtain α-xanthyl ketones from α-diazoketones is described. The reaction proceed through a protonation/nucleophilic substitution sequence with p-toluenesulfonic acid and potassium ethyl xanthogenate as nucleophile. As α-diazoketones can be readily synthesized from ubiquitous carboxylic acids, a broad variety of xanthates can be obtained, including those from natural occurring substrates

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Stereoselective synthesis of CD-ring precursors of vitamin D derivatives

Cited by 24 publications

References 79 publications

Synthesis of marmycin A and investigation into its cellular activity

Synthesis of marmycin A and investigation into its cellular activity

Surface‐Initiated RAFT/MADIX Polymerization on Xanthate‐Coated Iron Oxide Nanoparticles

α-Xanthylmethyl Ketones from α-Diazo ketones

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