DETECTION, SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (-NORTAYLORIONE, ANEW TERPENE FROM ARTEMISIA-ANNUA())

Nortaylorione a new nor-sesquiterpene, was identified among minor comp onents of Artemisia annua (hybrid plants) essential oil. Its relative and absolute configurations were determined by GC and GC/MS equipped w ith a chiral column and coinjecting the essential oil with synthetic s tandards (racemic and homochiral), obtained in a few steps from commer cial reagents. Pauson-Khand reaction was used as the key reaction in b oth synthetic pathways. The new natural product, named (+)-nortaylorio ne, is the (1'S)-cis-2-[2',2'-dimethyI-3'-(3 ''-butanon-l ''-yl)-cyclo propyl]2-cyclopenten-1-one. (C) 1997 Elsevier Science Ltd.