Isolating Friedelin from Cork and Reducing It to Friedelinol and Epifriedelinol. A Project Involving NMR Spectrometry and Molecular Modeling

LeFevre, Joseph W.; McNeill, Kristin I.; Moore, Janet

doi:10.1021/ed078p535

Cited by 11 publications

(8 citation statements)

References 11 publications

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“…63 Finally, hemicellulose B-2 is composed of xylose, arabinose, glucose, galactose, 4-O-methylglucuronic acid and rhamnose. 64 It is also possible to evaluate the polysaccharide composition by means of enzymatic hydrolysis, which gives different results: 63 . 9% of glucose, 7 .…”

Section: Polysaccharidesmentioning

confidence: 99%

Cork: properties, capabilities and applications

Silva¹,

Sabino²,

Fernandes³

et al. 2005

International Materials Reviews

537

352

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Cork is a natural, renewable, sustainable raw material that has been used for many centuries. As a result of this very long term interest, the scientific literature on cork is extensive. The present review focuses on the chemical composition, physical and mechanical properties of cork and on its products and sub-products. The substantial efforts to fully characterise cork, as well as new developments and evolving research, are reviewed, beginning with its histology, growth and morphology (at macro-and microscales). The chemical structure is analysed in detail, covering both the materials that form the wall structure and the low molecular weight, extractable components. The unique properties of cork are discussed and correlated with current knowledge on morphology and chemical structure. Finally, the important industrial applications of cork are reviewed, in the context of research to provide cork with novel, high added-value applications.

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Section: Polysaccharidesmentioning

confidence: 99%

Cork: properties, capabilities and applications

Silva¹,

Sabino²,

Fernandes³

et al. 2005

International Materials Reviews

537

352

View full text Add to dashboard Cite

show abstract

“…8 Finally, LeFevre and co-workers described a laboratory experiment in which friedelin (3, Figure 1) is isolated from cork and reduced to the corresponding alcohol. 9 To determine which diastereomer is formed in this reaction, force field minimizations are used to determine optimal dihedral angles for each diastereomer, followed by application of the Karplus equation 10 to calculate the corresponding coupling constants expected for each diastereomer. Comparing these coupling constants to the experimental data allows students to identify which diastereomer was formed preferentially.…”

Section: ■ Introductionmentioning

confidence: 99%

“…O’Shea and co-workers published an exercise wherein various essential oils are isolated from spices, and high performance liquid chromatography (HPLC) and gas chromatography–mass spectrometry (GC–MS) are then used to deduce the spice associated with each oil . Finally, LeFevre and co-workers described a laboratory experiment in which friedelin ( 3 , Figure ) is isolated from cork and reduced to the corresponding alcohol . To determine which diastereomer is formed in this reaction, force field minimizations are used to determine optimal dihedral angles for each diastereomer, followed by application of the Karplus equation to calculate the corresponding coupling constants expected for each diastereomer.…”

Section: Introductionmentioning

confidence: 99%

Reassigning the Structures of Natural Products Using NMR Chemical Shifts Computed with Quantum Mechanics: A Laboratory Exercise

et al. 2014

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An applied computational chemistry laboratory exercise is described in which students use modern quantum chemical calculations of chemical shifts to assign the structure of a recently isolated natural product. A pre/post assessment was used to measure student learning gains and verify that students demonstrated proficiency of key learning objectives. ■ INTRODUCTIONThe elucidation of the structures (connectivity, relative stereochemistry, and configuration) of complex natural products is a challenging endeavor despite huge leaps in spectroscopic technology over the past century. Among the most useful tools for structure elucidation is nuclear magnetic resonance (NMR) spectroscopy. Recently, Breton and Reynolds presented an excellent review of the various tools natural products chemists utilize in assigning structures, with an emphasis on how the use of NMR spectroscopy has evolved over the years. 1 Previous work has demonstrated the utility of NMR computations, in conjunction with traditional analyses, in the assignment and reassignment of natural product structures. 2 Upper-division undergraduate chemistry courses generally do not expose students to this important aspect of NMR spectroscopy. Herein, a computer-based laboratory experiment is described that highlights this application of NMR spectroscopy, as well as the utility of quantum chemical calculations, through a brief project that models a state-of-the-art research project in the field of structural elucidation. This exercise is appropriate for students who have been introduced to the basic concepts of NMR spectroscopy and quantum mechanics; advanced knowledge of neither is required. Consequently, this lab exercise could be adapted for an undergraduate or graduate organic, natural products, quantum chemistry, or applied theoretical chemistry course (and perhaps others).Key features of the approach include the following: 1. The exercise described is derived from recent reports on current research problems in the natural products and applied theoretical chemistry fields. 2. The exercise is designed to encourage hypothesis generation and testing, experimental design, discovery, active learning, 3 and data analysis by utilizing many activities and questions that involve higher order cognitive processes. 4 3. The exercise provides a basic framework for applying NMR calculations to structure elucidation that is suitable for a 1−2 h laboratory period, but possible extensions appropriate for different courses, cohorts of students, and instructors are provided in the Supporting Information.

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“… − They have well demonstrated the incorporation of either biobased reactants or reagents, and some serve to demonstrate the total synthesis of one natural product into another . Common are laboratories that detail the isolation and identification of biological molecules that may serve the introductory organic chemistry class, − but a rare few detail transformations of these molecules , truly following the biorefinery model by identifying cheap and readily available starting materials for use. Beyond these, there exists a set of laboratories, polymerizations, and interdisciplinary experiments that detail the development of materials from biomass.…”

mentioning

confidence: 99%

Biobased Organic Chemistry Laboratories as Sustainable Experiment Alternatives

Silverman¹

2016

J. Chem. Educ.

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As nonrenewable resources deplete and educators seek relevant interdisciplinary content for organic chemistry instruction, biobased laboratory experiments present themselves as potential alternatives to petroleum-based transformations, which offer themselves as sustainable variations on important themes. Following the principles of green chemistry and the powerful biorefinery model it is possible to create pedagogically sound and modern laboratory experiments employing readily available renewable reactants and reagents to convey important organic chemistry principles. In a reverse approach compared to total synthesis, these experiments should serve to not only make the undergraduate organic chemistry laboratory more green and sustainable but also educate the next generation with both historically important developments and cutting-edge research.

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Isolating Friedelin from Cork and Reducing It to Friedelinol and Epifriedelinol. A Project Involving NMR Spectrometry and Molecular Modeling

Cited by 11 publications

References 11 publications

Cork: properties, capabilities and applications

Cork: properties, capabilities and applications

Reassigning the Structures of Natural Products Using NMR Chemical Shifts Computed with Quantum Mechanics: A Laboratory Exercise

Biobased Organic Chemistry Laboratories as Sustainable Experiment Alternatives

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