Accurate prediction of the optical rotation and NMR properties for highly flexible chiral natural products

作者：Hashmi Muhammad Ali; Andreassend Sarah K; Keyzers Robert A; Lein Matthias^*

来源：Physical Chemistry Chemical Physics, 2016, 18(35): 24506-24510.

DOI：10.1039/c6cp04828e

Despite advances in electronic structure theory the theoretical prediction of spectroscopic properties remains a computational challenge. This is especially true for natural products that exhibit very large conformational freedom and hence need to be sampled over many different accessible conformations. We report a strategy, which is able to predict NMR chemical shifts and more elusive properties like the optical rotation with great precision, through step-wise incremental increases of the conformational degrees of freedom. The application of this method is demonstrated for 3-epi-xestoaminol C, a chiral natural compound with a long, linear alkyl chain of 14 carbon atoms. Experimental NMR and [alpha](D) values are reported to validate the results of the density functional theory calculations.

• 出版日期2016