4,4′-[(2R*,3R*,4R*,5R*)-3,4-Dimethyl­tetra­hydro­furan-2,5-di­yl]diphenol

Favela-Hernández, J.M. de J.; Camacho-Corona, M. del R.; Bernès, S.; Flores-Alamo, M.

doi:10.1107/S1600536812039359

Acta Crystallographica Section E

Structure Reports Online

Volume 68, Part 10 (October 2012)

organic compounds

mw2082 scheme

Acta Cryst. (2012). E68, o3019-o3020 [ doi:10.1107/S1600536812039359 ]

4,4'-[(2R,3R,4R,5R)-3,4-Dimethyltetrahydrofuran-2,5-diyl]diphenol

J. M. de J. Favela-Hernández, M. del R. Camacho-Corona, S. Bernès and M. Flores-Alamo

Abstract: The title molecule, C₁₈H₂₀O₃, is a furanoid lignan extracted from the leaves of Larrea tridentata. The relative absolute configuration for the four chiral centers was established, showing that this compound is 4-epi-larreatricin, which has been previously reported in the literature. The molecule displays noncrystallographic C₂ symmetry, with the methyl and phenol substituents alternating above and below the mean plane of the furan ring. The conformation of this ring is described by the pseudorotation phase angle P = 171.3° and the maximum out-of-plane pucker [nu] _m = 37.7°. These parameters indicate that the furan ring adopts the same conformation as the ribose residues in B-DNA. The packing is dominated by intermolecular O-HO hydrogen bonds. The phenol hydroxy groups form chains in the [110] direction and these chains interact via O-HO(furan) contacts.