A Macrocyclic Dimeric Diterpene with a C2 Symmetry Axis
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- 作者：J. Jes煤s Manr铆quez-Torres ; J. Mart铆n Torres-Valencia ; Ren茅 Vel谩zquez-Jim茅nez ; Alejandro Valdez-Calder贸n ; Jos茅 G. Alvarado-Rodr铆guez ; Carlos M. Cerda-Garc铆a-Rojas ; Pedro Joseph-Nathan
- 刊名：Organic Letters
- 出版年：2013
- 出版时间：September 20, 2013
- 年：2013
- 卷：15
- 期：18
- 页码：4658-4661
- 全文大小：254K
- 年卷期：v.15,no.18(September 20, 2013)
- ISSN：1523-7052
文摘
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鈥?i>S,7鈥?i>S,8鈥?i>R,9鈥?i>R,10鈥?i>S,17鈥?i>S)-7,8:7,17鈥?16,17:17,7鈥?7鈥?8鈥?16鈥?17鈥?hexaepoxy-7,8-seco-7鈥?8鈥?seco-dicassa-13,13鈥?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.