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Absolute Configuration Assignment to Chiral Natural Products by Biphenyl Chiroptical Probes: The Case of the Phytotoxins Colletochlorin A and Agropyrenol
journal contribution
posted on 2020-02-24, 20:19 authored by Ernesto Santoro, Stefania Vergura, Patrizia Scafato, Sandra Belviso, Marco Masi, Antonio Evidente, Stefano SuperchiThe application of flexible biphenyls
as chiroptical probes for
the absolute configuration assignment to chiral natural products is
described. The method is straightforward and reliable and can be applied
to conformationally mobile and ECD silent compounds, not treatable
by computational analysis of chiroptical data. By this approach, the
(6′R) absolute configuration of the phytotoxin
colletochlorin A (1) was confirmed, while the absolute
configuration of the phytotoxin agropyrenol (2), previously
assigned by the NMR Mosher method, was revised and assigned as (3′S,4′S). Moreover, with the biphenyl
method the configurational assignment can be obtained simply by the
sign of a diagnostic Cotton effect at 250 nm in the ECD spectrum,
thus allowing application without the need of advanced knowledge of
chiroptical spectroscopy and computational protocols.
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chiroptical probesBiphenyl Chiroptical ProbesECD spectrumphytotoxin colletochlorinAbsolute Configuration Assignmentchiroptical spectroscopy250 nmchiroptical dataapplicationChiral Natural Productsconfiguration assignmentbiphenyl methodconfigurational assignmentCotton effectphytotoxin agropyrenolPhytotoxins ColletochlorinNMR Mosher method
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