Assignment of Relative and Absolute Configuration by Organic Synthesis -Universal NMR Database Approach: Logic, Development, and Application

By: Yoshito Kishi

Department of Chemistry and Chemical Biology, Harvard University

With use of the marine natural product palytoxin as an example, we shall review the stereochemistry assignment by organic synthesis. We then discuss how this work has evolved to the universal NMR database approach, which allows assignment of the relative and absolute configuration of unknown compounds without degradation and/or derivatization. To illustrate this approach, we shall use mycolactone A/B, the causative toxin of Buruli ulcer, as an example.