ol9b03964_si_001.pdf (3.21 MB)
Structure and Conformation of Zosteraphenols, Tetracyclic Diarylheptanoids from the Seagrass Zostera marina: An NMR and DFT Study
journal contribution
posted on 2019-12-13, 19:30 authored by Laura Grauso, Yan Li, Silvia Scarpato, Oleksandr Shulha, Lucie Rárová, Miroslav Strnad, Roberta Teta, Alfonso Mangoni, Christian ZidornZosteraphenols, 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.