Structure and Conformation of Zosteraphenols, Tetracyclic Diarylheptanoids from the Seagrass Zostera marina: An NMR and DFT Study

Zosteraphenols, two new tetracyclic diarylheptanoids were isolated from the seagrass Zostera marina. The rotameric equilibrium of the strained tetracyclic structures, involving a diastereomeric minor rotamer with opposite axial chirality, resulted in coalescent NMR spectra. Although the elusive mino...

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Published in:Organic letters 2020-01, Vol.22 (1), p.78-82
Main Authors: Grauso, Laura, Li, Yan, Scarpato, Silvia, Shulha, Oleksandr, Rárová, Lucie, Strnad, Miroslav, Teta, Roberta, Mangoni, Alfonso, Zidorn, Christian
Format: Article
Language:English
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Summary:Zosteraphenols, two new tetracyclic diarylheptanoids were isolated from the seagrass Zostera marina. The rotameric equilibrium of the strained tetracyclic structures, involving a diastereomeric minor rotamer with opposite axial chirality, resulted in coalescent NMR spectra. Although the elusive minor rotamer was only characterized with 1H chemical shifts, the excellent agreement between experimental and DFT-calculated chemical shifts of both rotamers unequivocally supported this analysis. Absolute configuration of zosteraphenols was determined by DFT prediction of their ECD spectra.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03964