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Open AccessArticle

Application of Computational Chemical Shift Prediction Techniques to the Cereoanhydride Structure Problem—Carboxylate Complications

Department of Chemistry, University of California—Davis, 1 Shields Avenue, Davis, CA 95616, USA
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Mar. Drugs 2017, 15(6), 171; https://doi.org/10.3390/md15060171
Received: 20 March 2017 / Revised: 2 June 2017 / Accepted: 8 June 2017 / Published: 12 June 2017
(This article belongs to the Special Issue Structural Techniques in Natural Products Drug Discovery)
Despite the vast array of techniques available to modern-day chemists, structural misassignments still occur. These misassignments are often only realized upon attempted synthesis, when the spectra of synthesized products do not match previously reported spectra. This was the case with marine natural product cereoanhydride. The originally proposed 7-membered ring anhydride (1) was shown to be incorrect, although a likely precursor to the correct structure (2) in both its laboratory synthesis and biosynthesis. Herein, in addition to showing how NMR computations could have been used to arrive at the correct structure, we show that the conversion of 1 to 2 is indeed energetically viable, and we highlight complications in predicting NMR chemical shifts for molecules with acidic protons. View Full-Text
Keywords: computational NMR; natural products; chemical shifts computational NMR; natural products; chemical shifts
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Saunders, C.M.; Tantillo, D.J. Application of Computational Chemical Shift Prediction Techniques to the Cereoanhydride Structure Problem—Carboxylate Complications. Mar. Drugs 2017, 15, 171.

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