A Macrocyclic Dimeric Diterpene with a C2 Symmetry Axis

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.