Synthesis of anti-Helicobacter pylori sesquiterpene employing tandem radical cyclization, and determination of the absolute configuration of the natural product

Abstract

Both enantiomers of (Z)-2β-hydroxy-14-hydro-β-santalol, a potent anti-H. pylori agent, were synthesized and the absolute configuration of the natural product was determined to be 1R,2S,3R,4S. The bicyclo[2.2.1]heptane skeleton was efficiently constructed employing tandem radical cyclization of tethered precursor. Both enantiomers were prepared via optical resolution of racemic intermediate.