Despite continued development of spectroscopic and crystallographic techniques the structural elucidation of complex natural products remains a challenging endeavour in which misassignments are not uncommon. Recently, the use of high-level computation to calculate the spectroscopic properties of organic molecules (particularly NMR chemical shifts) has emerged as a new strategy for structure determination. Combining our computational approach with biosynthetic considerations has given us the ability to reliably predict the absolute configuration of a number of elusive marine natural products, leading to proof via total synthesis.Computational approaches towards understanding the stereo- and regiochemical outcome in fundamental types of organocatalyzed carbocyclizations are also explored in this talk: we have developed qualitative and quantitative models which explain how it is possible to subvert the traditional rules governing ring-closure through changes in substrate or catalyst

Computational discoveries of organic stereostructures and selectivities

248th National Meeting (2014)

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