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Total assignment of 1H and 13C NMR data for the sesquiterpene lactone 15-deoxygoyazensolide

✍ Scribed by Vladimir Constantino Gomes Heleno; Antônio Eduardo Miller Crotti; Mauricio Gomes Constantino; Norberto Peporine Lopes; João Luis Callegari Lopes

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
97 KB
Volume
42
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

We describe a complete analysis of the ^1^H and ^13^C spectra of the anti‐inflamatory, schistossomicidal and trypanosomicidal sesquiterpene lactone 15‐deoxygoyazensolide. This lactone, with a structure similar to other important ones, was studied by NMR techniques such as COSY, HMQC, HMBC, __J__res and NOE experiments. The comparison of the data with some computational results led to an unequivocal assignment of all hydrogen and carbon chemical shifts, even eliminating some previous ambiguities. We were able to determine all hydrogen coupling constants (J) and signal multiplicities and to confirm the stereochemistry. A new method for the determination of the relative position of the lactonization and the position of the ester group on a medium‐sized ring by NMR was developed. Copyright © 2004 John Wiley & Sons, Ltd.

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