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  • Title: A macrocyclic dimeric diterpene with a C2 symmetry axis.
    Author: Manríquez-Torres JJ, Torres-Valencia JM, Velázquez-Jiménez R, Valdez-Calderón A, Alvarado-Rodríguez JG, Cerda-García-Rojas CM, Joseph-Nathan P.
    Journal: Org Lett; 2013 Sep 20; 15(18):4658-61. PubMed ID: 23937093.
    Abstract:
    An unprecedented macrocyclic dimeric diterpene containing a C2 symmetry axis was isolated from Acacia schaffneri . This compound, named schaffnerine, was characterized as (5S,7S,8R,9R,10S,17S,5'S,7'S,8'R,9'R,10'S,17'S)-7,8:7,17':16,17:17,7':7',8':16',17'-hexaepoxy-7,8-seco-7',8'-seco-dicassa-13,13'-diene (1) from its spectroscopic data. Comparison of its experimental vibrational circular dichroism spectrum with that calculated using density functional theory, at the B3LYP/DGDZVP level, assigned its preferred conformation and absolute configuration. The latter was confirmed by evaluation of the Flack and Hooft parameters obtained after single-crystal X-ray diffraction analysis.
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