DETECTION, SYNTHESIS AND ABSOLUTE CONFIGURATION OF (+)-NORTAYLORIONE, A NEW TERPENE FROM ARTEMISIA ANNUA

Abstract 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)-cyclopropyl]-2-cyclopenten-1-one.