The Use of TMS for Determining the Absolute Configuration of Natural Products Bearing Hydroxyl Groups

Compounds isolated from natural sources continue to make invaluable contributions across many fields of chemistry. Structures elucidated and reported in the literature often serve as starting points for the total synthesis of bioactive compounds. In this painstaking process of separation and structural elucidation, one of the most complex steps is the determination of absolute configuration. In this work we present a combination of a simple molecular modification, which is fast, robust and selective, with traditional single-crystal X-ray diffraction to achieve high precision in determining absolute configuration. The method can be employed on a wide variety of compounds bearing at least one hydroxylic group, which includes a significant proportion of natural products.