Theoretical and experimental study of the absolute configuration of helical structure of (2R,3S)-Rubiginone A2 analog |
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Authors: | Bei-Dou Zhou Jie Ren Xin-Chun Liu Hua-Jie Zhu |
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Institution: | 1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academic of Sciences, 132# Lanhei Rd., Kunming 650204, PR China;2. College of Life Science, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding 071002, PR China;3. Graduate University of CAS, Beijing 100049, PR China |
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Abstract: | A novel analogue of (2R,3S)-Rubiginone A2 was synthesized as a chiral helical model compound via an eight-step procedure (2.7% overall yield). Quantum methods, such as density functional theory (DFT) at different basis sets of 6-311+(d), 6-311++G(2d,p), were used to compute its optical rotation and electronic circular dichroism at the B3LYP/6-311++G(2d,p) level in the gas phase and in solution using PCM model, respectively. UV corrections were performed in electronic circular dichroism (ECD) simulations to match the experimental ECD well. The suitable computational methods, e.g., B3LYP/6-311++G(2d,p)//B3LYP/6-311++G(2d,p) in the gas phase using zero-point energy in Boltzmann statistics, were found and suggested for optical rotation and circular dichroism computations that can be used for absolute configuration determination of chiral helical compounds. |
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