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

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• 作者：Giacomo Saielli ; K. C. Nicolaou ; Adrian Ortiz ; Hongjun Zhang ; Alessandro Bagno
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：April 20, 2011
• 年：2011
• 卷：133
• 期：15
• 页码：6072-6077
• 全文大小：837K
• 年卷期：v.133,no.15(April 20, 2011)
• ISSN：1520-5126

文摘

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.