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Vibrational Circular Dichroism Absolute Configuration Determination of Natural Products

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Progress in the Chemistry of Organic Natural Products 100

Part of the book series: Progress in the Chemistry of Organic Natural Products ((POGRCHEM,volume 100))

Abstract

The most widely used physical methods for the chemical analysis of natural products are currently well established, although in the case of vibrational circular dichroism (VCD), this is not yet the case. The first VCD experiments were performed only about 40 years ago, and it took some 20 additional years for the development of sufficiently sensitive instrumentation for these types of measurements, since VCD signals are three to four orders of magnitude less sensitive than infrared bands. In addition, it is less than 20 years since chemists started to have routine access to computers that allowed adequate quantum chemical calculations for this type of study. Thus, most applications of VCD to the study of sesquiterpenes, diterpenes, and molecules of similar size have been performed in the present century. Consequently, the main objective of this chapter is to provide some background and to show the use of circularly polarized infrared radiation for the determination of absolute configuration, and in some cases of the configuration of a specific chiral center, in natural products. This is a task that, in some cases, has been almost impossible to complete using other spectroscopic methods. VCD relies mostly on the comparison of an experimental spectrum, obtained in the mid infrared region of the electromechanical spectrum, with a spectrum obtained by density functional theory calculations, a situation that requires a detailed knowledge of the lower energy conformers of the particular molecule being studied.

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Acknowledgements

We are indebted to the editors, Professors Heinz Falk and Douglas Kinghorn, for all the valuable suggestions they made for the preparation of this chapter, and thank CONACYT-Mexico for financial support through grant 152994.

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    Pedro Joseph-Nathan & Bárbara Gordillo-Román

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Correspondence to Pedro Joseph-Nathan .

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  1. College of Pharmacy, The Ohio State University, Columbus, Ohio, USA

    A. D. Kinghorn

  2. Institut für Organische Chemie, Johannes-Keppler-Universität Linz, Linz, Austria

    H. Falk

  3. Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan

    J. Kobayashi

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Joseph-Nathan, P., Gordillo-Román, B. (2015). Vibrational Circular Dichroism Absolute Configuration Determination of Natural Products. In: Kinghorn, A., Falk, H., Kobayashi, J. (eds) Progress in the Chemistry of Organic Natural Products 100. Progress in the Chemistry of Organic Natural Products, vol 100. Springer, Cham. https://doi.org/10.1007/978-3-319-05275-5_4

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