Addressing the Stereochemistry of Complex Organic Molecules by Density Functional Theory-NMR: Vannusal B in Retrospective

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 g...

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Published inJournal of the American Chemical Society Vol. 133; no. 15; pp. 6072 - 6077
Main Authors Saielli, Giacomo, Nicolaou, K. C, Ortiz, Adrian, Zhang, Hongjun, Bagno, Alessandro
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 20.04.2011
Subjects
Ciliophora - chemistry
Magnetic Resonance Spectroscopy - methods
Quantum Theory
Spiro Compounds - chemistry
Stereoisomerism
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Summary: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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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja201108a