32 research outputs found

    Palladium-catalysed annulation reaction of allenyltins with beta-iodo vinylic acids: selective synthesis of alpha-pyrones

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    Palladium-catalysed regio- and stereoselective annulation of allenyl stannanes by beta-iodo vinylic acids gives the corresponding alpha-pyrones in high yields. This annulation most probably proceeds through a Stille reaction/cyclisation sequence

    An Efficient Synthesis of New 7-Trifluoromethyl-2,5-disubstituted Pyrazolo 1,5-a pyrimidines

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    International audienceA novel two-step synthesis of trifluoromethylated 3,5-disubstituted pyrazolo[1,5- a ]pyrimidines is reported from 3-aminopyrazoles and ethyl 4,4,4-trifluorobut-2-ynoate. The synthetic route begins with the one-pot synthesis of 7-trifluoromethylated pyrazolo[1,5- a ]pyrimidin-5-ones by condensation of 3-aminopyrazoles with a fluorinated alkyne. The products obtained are used as building blocks to synthesize directly, with excellent yields via C-O bond activation, a library of new fluorinated 3,5-disubstituted pyrazolo[1,5- a ]pyrimidines of biological interest. This operation efficiently allows C-C, C-N and C-S bond formation

    Synthesis and Reactivity of beta,gamma-Dihalogenated Unsaturated Acids: Application to the Synthesis of 4-Substituted 5H-Furan-2-ones

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    International audiencebeta,gamma-Dihalogenated unsaturated acids were prepared regio- and stereoselectively from allenic acid, and some aspects of their reactivities were studied

    Copper-mediated cross-coupling of functionalized arylmagnesium reagents with functionalized alkyl and benzylic halides

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    Functionalized arylmagnesium halides, prepared via an iodine−magnesium exchange, undergo a smooth cross-coupling reaction with functionalized primary alkyl iodides and benzylic bromides in the presence of CuCN·2LiCl, either in stoichiometric (with trimethyl phosphite as an additive) or catalytic quantities

    Total synthesis of N<sup>14</sup>-desacetoxytubulysin H

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    Equation presented The N14-desacetoxy analogue of tubulysin H was prepared in 20 steps and 2.1% overall yield. Our strategy features a thiazole anion addition to assemble the tubuvaline residue at the C(10)-C(11) bond, as well as acylations at N5, N14, and N 17. This iterative coupling approach, as well as the removal of the labile N,O-acetal at N14, enables the synthesis of analogues for detailed studies of structure-activity relationships in this family of potent tubulin disrupters. © 2007 American Chemical Society
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