Optimization of Grignard ring-opening of α-brominated dioxolanes for the preparation of β-hydroxy-protected vinyl ethers by a three-step one-pot procedure

Meynier, André; Letribot, Boris; Bayle, Martine; Mounetou, Emmanuelle; Chezal, Jean‐Michel

doi:10.1016/j.tetlet.2012.08.144

Cited by 6 publications

(3 citation statements)

References 19 publications

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“…To a solution of the mesylates 4a-c and DIPEA (1.5 eq.) in anhydrous MeCN (0.05 M) was added N-(2-ethylaminoethyl)-6-iodoquinoxaline-2-carboxamide 19 (1.5 eq.). The mixture was stirred for a different time at a different temperature for each compound then poured into sat.…”

Section: Methodsmentioning

confidence: 99%

“…Tri-n-butylstannane precursor 3a was successfully prepared by palladium(II)-catalysed Stille coupling recation of the previously synthesized iodo-analog 2a 10,19 with hexabutylditin in refluxing dioxane (Scheme 1). 18 However, under similar conditions, the reaction of the PEGylated derivatives 2b and 2c 10 with hexabutylditin did not give the desired tri-n-butylstannyled compounds, but instead led to the formation of the hydrodeiodinated products.…”

Section: Synthesismentioning

confidence: 99%

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PEGylation enhances the tumor selectivity of melanoma-targeted conjugates

et al. 2015

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In the development of our melanoma-selective delivery approach, three preselected conjugates of 5-iodo-2'-deoxyuridine (IUdR) to the ICF01012 melanoma-carrier were radiolabelled with iodine-125, and their in vivo distribution profile was determined. A radioiodination method for the conjugate 1a and its PEGylated derivatives 1b-c was developed via electrophilic iododestannylation in good radiochemical yield with excellent radiochemical purity (>99%). When administered to melanoma-bearing mice, the PEGylated conjugates exhibited an increased tumour uptake with a prolonged residence time. PEGylation also resulted in enhanced tumour selectivity compared with the non-PEGylated parent. These characteristics support further development of this model to achieve maximal concentration of anticancer therapeutics at the local site of action and minimize distribution to non-targeted sites.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

PEGylation enhances the tumor selectivity of melanoma-targeted conjugates

et al. 2015

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“…Therefore, a variety of methods have been reported for the synthesis of vinyl ethers, including modified transetherification 11 , addition-elimination reactions 12 , carbonyl olefinations 13 , additions of alcohol to triple bonds 14 and metal-catalyzed coupling or transfer reactions 15 . However, classical synthesis of vinyl ethers has shown serious limitations, such as the use of strong acids or bases 16,17 , expensive catalyse metals 18 and high temperatures 19 . Therefore, the need to implement new inexpensive and easy methodologies to produce functional vinyl ethers remains challenging.…”

Section: Introductionmentioning

confidence: 99%