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The study of natural and synthetic organic compounds has been investigated. The use of one-dimensional and two-dimensional NMR methods as a method for rapidly assigning structures was demonstrated. Structural elucidation was performed on unknown side-products in synthetic sequences to conclusively determine what reactions had taken place. Steps toward a biomimetic synthesis of the alkaloid, dihydrocadambine, were carried out. The isolation of the natural product precursor to this alkaloid, secologanin, was first performed. In the course of isolating secologanin, two other natural products, loganin and sweroside were also isolated and structurally elucidated. The intermediates in the attempted synthesis of dihydrocadambine were also examined. Finally, NMR methods were applied to characterization of diterpene and sesquiterpene natural products isolated in the Caribbean. Eleven of the natural products investigated were determined to be novel.
This book is aimed at informing organic chemists and natural products chemists on the use of NMR for structure elucidation to enable them to ensure they yield the most reliable possible data in the minimum possible time. It covers the latest pulse sequences, acquisition and processing methods, practical areas not covered in most texts e.g. detailed consideration of the relative advantages and disadvantages of different pulse sequences, choosing acquisition and processing parameters to get the best possible data in the least possible time, pitfalls to avoid and how to minimize the risks of getting wrong structures. Useful in industrial, pharma or research environments, this reference book is for anyone involved with organic chemistry research and, in particular, natural products research requiring advice for getting the best results from the NMR facilities.
A blend of theory and practical advice, Modern NMR Techniques for Synthetic Chemistry illustrates how NMR spectroscopy can be used to determine the abundance, size, shape, and function of organic molecules. It provides you with a description the NMR technique used (more pictorial than mathematical), indicating the most common pulse sequences, some practical information as appropriate, followed by illustrative examples. This format is followed for each chapter so you can skip the more theoretical details if the practical aspects are what interest you. Following a discussion of basic parameters, the book describes the utility of NMR in detecting and quantifying dynamic processes, with particular emphasis on the usefulness of saturation-transfer (STD) techniques. It details pulsed–field gradient approaches to diffusion measurement, diffusion models, and approaches to ‘inorganic’ nuclei detection, important as many synthetic pathways to new organics involve heavier elements. The text concludes with coverage of applications of NMR to the analysis of complex mixtures, natural products, carbohydrates, and nucleic acids—all areas of activity for researchers working at the chemistry-life sciences interface. The book’s unique format provides some theoretical insight into the NMR technique used, indicating the most common pulse sequences. The book draws upon several NMR methods that are resurging or currently hot in the field and indicates the specific pulse sequence used by various spectrometer manufacturers for each technique. It examines the analysis of complex mixtures, a feature not found in most books on this topic.
The first volume in a two-part set that discusses contemporary NMR approaches for the structure elucidation of natural products. It covers optimized hardware and experimental approaches.
The Ghanian plant Cryptolepis sanguinolenta is the source of a series of fascinating indoloquinoline alkaloids. The most unusual member of this alkaloid series was initially proposed to be a spiro nonacyclic structure, named cryptospirolepine, and was elucidated in 1993 based on the technologies available at that time. There were, however, several annoying attributes to the structure that bothered analysts for the ensuing 22 years. During the two decades that followed the initial work there have been enormous developments in NMR technology. Using new experimental approaches, specifically homodecoupled 1,1- and 1,n-HD-ADEQUATE NMR experiments developed in 2014, the structure of only a 700 μg sample of cryptospirolepine has been revised and is shown on the cover of this volume. The confluence of the NMR technological and methodological advances that allowed the revision of the structure of cryptospirolepine using a submilligram sample seems a fitting example for this book, which is dedicated to the NMR characterization of various classes of natural products. Volume 2 considers data processing and algorithmic based analyses tailored to natural product structure elucidation and reviews the application of NMR to the analysis of a series of different natural product families including marine natural products, terpenes, steroids, alkaloids and carbohydrates. Volume 1 discusses contemporary NMR approaches including optimized and future hardware and experimental approaches to obtain both the highest quality and most appropriate spectral data for analysis. These books, bringing together acknowledged experts, uniquely focus on the combination of experimental approaches and modern hardware and software applied to the structure elucidation of natural products. The volumes will be an essential resource for NMR spectroscopists, natural product chemists and industrial researchers working on natural product analysis or the characterization of impurities and degradation products of pharmaceuticals that can be as scarce as natural product samples.
NMR Spectroscopy Explained : Simplified Theory, Applications and Examples for Organic Chemistry and Structural Biology provides a fresh, practical guide to NMR for both students and practitioners, in a clearly written and non-mathematical format. It gives the reader an intermediate level theoretical basis for understanding laboratory applications, developing concepts gradually within the context of examples and useful experiments. Introduces students to modern NMR as applied to analysis of organic compounds. Presents material in a clear, conversational style that is appealing to students. Contains comprehensive coverage of how NMR experiments actually work. Combines basic ideas with practical implementation of the spectrometer. Provides an intermediate level theoretical basis for understanding laboratory experiments. Develops concepts gradually within the context of examples and useful experiments. Introduces the product operator formalism after introducing the simpler (but limited) vector model.
For several years we have been organizing seminars and workshops on the application of modem one and two-dimensional NMR methods at the faculty of chemistry in the Ruhr-University Bochum, FRG, and elsewhere, addressing researchers and graduate students who work in the field of organic and natural products chemistry. In 1987, we wrote a workbook (StrukturaufkUirung mit modemer NMR-Spektroskopie, Steinkopff, Darmstadt, FRG, 1988) in German language based on our experience in these courses. Many of the exercises described therein have been used in such courses and some of them have been shaped by the participants to a great extent. The response of readers and discussions with colleagues from many countries encouraged us to produce an English translation in order to make the book accessible to a wider audience. Moreover, the content has been increased from 20 exercise examples in the German, to 23 in the English version. This book could not have been written in the present form without the help of a number of col leagues and, therefore, we acknowledge gratefully the generous supply of samples from and useful discussions with B. Abegaz (Addis Ababa, Ethiopia), U.H. Brinker (Bingham, New York, USA), E.
"Nuclear Magnetic Resonance (NMR) Spectroscopy remains the foremost analytical technique for the structure elucidation of organic molecules and an indispensable tool for the synthetic, medicinal and natural product chemist. New techniques continue to emerge and the application of NMR methods continues to expand. High-Resolution NMR Techniques in Organic Chemistry is designed for use in academic and industrial NMR facilities, as a text for graduate-level NMR courses, and as an accessible reference for the chemist's or spectroscopist's desk."--BOOK JACKET.