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      Addressing the stereochemistry of complex organic molecules by density functional theory-NMR: vannusal B in retrospective.

      Journal of the American Chemical Society
      Ciliophora, chemistry, Magnetic Resonance Spectroscopy, methods, Quantum Theory, Spiro Compounds, Stereoisomerism

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          Abstract

          We have employed density functional theory (DFT) protocols to calculate the NMR properties of the vannusals, a class of natural products whose structures have been the subject of recent investigations. The originally assigned structure of vannusal B was revised after a long synthetic journey which generated a series of closely related diastereomers. In this work we show how DFT calculations based on density functionals and basis sets designed for the prediction of NMR spectra (M06/pcS-2 level of theory) can be used to reproduce the observed parameters, thereby offering to the synthetic chemist a useful tool to discard or accept putative structures of unknown organic molecules.

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          Author and article information

          Journal
          21438587
          3100668
          10.1021/ja201108a

          Chemistry
          Ciliophora,chemistry,Magnetic Resonance Spectroscopy,methods,Quantum Theory,Spiro Compounds,Stereoisomerism

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