A macrocyclic dimeric diterpene with a C2 symmetry axis.
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.
Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, km 4.5 Carretera Pachuca-Tulancingo, Mineral de la Reforma, Hidalgo, 42184 Mexico, and Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, México, D.F., 07000 Mexico.
J Jesús
JJ
Manríquez-Torres
J Martín
JM
Torres-Valencia
René
R
Velázquez-Jiménez
Alejandro
A
Valdez-Calderón
José G
JG
Alvarado-Rodríguez
Carlos M
CM
Cerda-García-Rojas
Pedro
P
Joseph-Nathan
D000045:Acacia / Q000737:chemistry*; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
C586465:(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; D004224:Diterpenes