Elucidating the Structural Isomerism of Fluorescent Strigolactone Analogue CISA‐1. Issue 6 (19th January 2015)

• Record Type: Journal Article
• Authors: Goossens, Hannelore; Heugebaert, Thomas S. A.; Dereli, Busra; Van Overtveldt, Melissa; Karahan, Ozlem; Dogan, Ilknur; Waroquier, Michel; Van Speybroeck, Veronique; Aviyente, Viktorya; Catak, Saron; Stevens, Christian V.
• Is Part Of: European journal of organic chemistry. Issue 6(2015)
• Page Start: 1211
• Page End: 1217
• Publication Date: 2015-01-19
• Subjects: Atropisomerism -- Lactones -- Conformation analysis -- Configuration determination -- Density functional calculations; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403457
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The synthesis of a new potent strigolactone analogue (CISA‐1), resulting in the formation of two interconverting structural isomers, which could not be identified, was recently reported. In the present study, a combined computational and experimental approach is used to identify the exact nature of these structural isomers. Although standard experimental techniques could not be used to determine the identity of the isomers, chromatographic methods excluded E / Z isomerisation. Computational 1 H NMR chemical shift values and DFT calculations on interconversion barriers strongly suggest that the CISA‐1 isomers were interconverting ( Z )‐configured atropisomers. Abstract : The occurrence of atropisomers among strigolactone analogues is reported for the first time. While the rate of interconversion for this specific derivative is sufficiently high to warrant full bioavailability, these findings are of high importance for the development of new analogues that could lead to stable atropisomers with different bioactivity.