The stereochemistry of glabrescol

The structure of glabrescol has been proposed and revised. Could the revised structure have been predicted without the need for total synthesis? Molecular modelling studies showed that the natural product structure proposed for glabrescol was not the most thermodynamically favourable form. When a lithium ion was incorporated, the natural product proved to be the lowest in energy of all symmetric isomers of glabrescol. Further modelling studies have led to the discovery of an asymmetric isomer lower in energy than the natural product when bound to a variety of ions.