Addressing the stereochemistry of complex organic molecules by density functional theory-NMR: vannusal B in retrospective |
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Authors: | Saielli Giacomo Nicolaou K C Ortiz Adrian Zhang Hongjun Bagno Alessandro |
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Institution: | Istituto per la Tecnologia delle Membrane del CNR, Unita? di Padova, Via Marzolo 1, 35131 Padova, Italy. |
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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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