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 minor rotamer was only characterized with 1 H 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.