Detection, synthesis and absolute configuration of (+)-nortaylorione, a new terpene from Artemisia annua

Article abstract of DOI:10.1016/S0957-4166(97)00169-9

Nortaylorione a new nor-sesquiterpene, was identified among minor components of Artemisia annua (hybrid plants) essential oil. Its relative and absolute configurations were determined by GC and GC/MS equipped with a chiral column and coinjecting the essential oil with synthetic standards (racemic and homochiral), obtained in a few steps from commercial reagents. Pauson-Khand reaction was used as the key reaction in both synthetic pathways. The new natural product, named (+)-nortaylorione, is the (1'S)-cis-2-[2' ,2'-dimethyl-3'-(3''-butanon-1''-yl)-cyctopropyl]-2-cyclopenten-1-one.