Stereochemical Analysis of Natural Products by Chiroptical Methods

The presentation will highlight the recent advance in application of the three common chiroptical methods, Electronic Circular Dichroism, Optical Rotatory Dispersion and Vibrational Circular Dichroism for the purpose of determining the absolute configurations (AC) of structurally diverse natural products. The discussion will focus on the emerging awareness regarding the advantages of using simultaneously more than one of these methods, and importantly, as a combined approach based on experimentally measured and theoretically simulated chiroptical properties. The recent studies will be illustrated by AC analysis of selected examples, among them, the irregular diterepene Anisotomenoic acid, the cruciferous phytoalexin Brasicanal C, the alkaloid Actinophyllic acid, and also the fungal and plant metabolites Scytolide, Phyllostin and Oxysporone.

Reference: Berova, N.; Ellestad; G. A.; Harada, N, Modern Methods in Natural Product Chemistry: Characterization by Circular Dichroism Spectroscopy, in Comprehensive Natural Products II Chemistry and Biology; Mander, L., Lui, H.-W, Eds.; Elsevier: Oxford, 2010; [Vol. 9 ] pp. 91 – 146; Comprehensive Chiroptical Spectroscopy” Berova, N; Polavarapu, P.; Nakanishi, K.; Woody, W. R. Eds. Wiley & Sons, Hoboken, NJ, 2012, Vol. 2, Chapters 4, 6, 10, 11 & 12; Mazzeo, G.; Santoro, E.; Andolfi, Cimmino, Troselj, P.; Petrovic, A.G.; Superchi, S.; Evidente, A.; Berova, N. J. Nat. Products, 2013, DOI: 10.1021/np300770 s