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...
| Publicado en: | Journal of the American Chemical Society Vol. 133; no. 15; pp. 6072 - 6078 |
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| Autores principales: | , , , , |
| Formato: | Artículo |
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American Chemical Society
4/20/2011
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=60793858&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 60793858 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 4/20/2011 vid: 133 iid: 15 pid: 997 pub: American Chemical Society artinfo: ui: 60793858 10.1021/ja201108a ppf: 6072 ppct: 6 formats: tig: atl: Addressing the Stereochemistry of Complex Organic Molecules by Density Functional Theory-NMR: Vannusal B in Retrospective. aug: au: Saielli, Giacomo Nicolaou, K. C. Ortiz, Adrian Hongjun Zhang Bagno, Alessandro affil: Istituto per la Tecnologia delle Membrane del CNR, Unità di Padova, Via Marzolo 1, 35131 Padova, Italy Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, United States Dipartimento di Scienze Chimiche, Università di Padova, via Marzolo 1, 35131 Padova, Italy su: Complex compounds Organic compounds Stereochemistry Density functionals Functional analysis Nuclear magnetic resonance spectroscopy sug: subj: Complex compounds Organic compounds Stereochemistry Density functionals Functional analysis Nuclear magnetic resonance spectroscopy ab: 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. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2011 holdings: @attributes: islocal: N |
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