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

Literature Information

Publication Date 2016-08-09
DOI 10.1039/C6CP04828E
Impact Factor 3.676
Authors

Muhammad Ali Hashmi


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Abstract

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 [α]D values are reported to validate the results of the density functional theory calculations.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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