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Issue 10, 2017
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Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

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Abstract

The first total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A have been accomplished using a nickel-catalyzed cross coupling of alkyl bromide with vinyl stannane as the final step. The other key steps include late-stage C(sp3)–H bromination, the oxidative cleavage of a diol to provide the requisite ketone and ester for schilancidilactones A and B, and Dieckmann-type condensation to generate the A ring of schilancitrilactone A and 20-epi-schilancitrilactone A.

Graphical abstract: Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

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Publication details

The article was received on 28 Jul 2017, accepted on 29 Aug 2017 and first published on 30 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC03293E
Citation: Chem. Sci., 2017,8, 7246-7250
  • Open access: Creative Commons BY-NC license
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    Total syntheses of schilancidilactones A and B, schilancitrilactone A, and 20-epi-schilancitrilactone A via late-stage nickel-catalyzed cross coupling

    H. Wang, X. Zhang and P. Tang, Chem. Sci., 2017, 8, 7246
    DOI: 10.1039/C7SC03293E

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