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A Macrocyclic Dimeric Diterpene with a C2 Symmetry Axis

Torres Valencia, J. Jesús Martín


A Macrocyclic Dimeric Diterpene with a C2 Symmetry AxisJ. Jesús Manríquez-Torres, J. Martín Torres-Valencia, René Velázquez-Jiménez, Alejandro Valdez-Calderón, José G. Alvarado-Rodríguez, Carlos M. Cerda-García-Rojas, and Pedro Joseph-Nathan, Org. Lett., 2013, 15 (18), pp 4658?4661DOI: 10.1021/ol401890v


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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