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Coniothyrione: anatomy of a structure revision
Author(s) -
Martin Gary E.,
Buevich Alexei V.,
Reibarkh Mikhail,
Singh Sheo B.,
Ondeyka John G.,
Williamson R. Thomas
Publication year - 2013
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.3952
Subject(s) - chemistry , reinterpretation , substituent , argument (complex analysis) , basis (linear algebra) , position (finance) , interpretation (philosophy) , density functional theory , substitution (logic) , stereochemistry , computational chemistry , geometry , computer science , biochemistry , mathematics , finance , economics , programming language , physics , acoustics
Coniothyrione is a xanthone‐derived antibiotic reported several years ago by researchers at Merck & Co. Inc. Revision of the position of the chloro substitution was recently proposed on the basis of empirical reinterpretation of the carbon chemical shift data and a hypothetical biosynthetic argument without the acquisition of any new spectral data to support the postulated change in substituent location. The originally published HMBC data lead to an equivocal assignment of the structure and do not provide a solid basis of support for either structure. Neural network 13 C chemical shift calculations and density functional theory calculations also led to undifferentiated structures. Definitive confirmation of the structure of coniothyrione based on the acquisition and interpretation of 1,1‐ADEQUATE and inverted 1 J CC 1,n‐ADEQUATE data is now reported. Copyright © 2013 John Wiley & Sons, Ltd.