A series of 18 new a,&unsaturated &&&substituted &lactones was synthesized as possible therapeutic agents. The majority of the compounds described contain an aryloxy grou in the pposition of the lactone ring, while those naturally occurring in P+er mat&ticwn all contain an alkoxy group in this position. Some of the lactones were hydrogenated by means of palladium-on-charcoal to the corresponding dihydro derivatives. The infrared absorption spectra of most of the synthesized compounds were also studied.
IPER METHYSTICUM Forst. of the family Peifiraceae is a shrub common to the islands of Indonesia where it is known in various dialects as kawa, kava, or ava. The rest of the kawa plant has been held in high esteem by the Polynesians from ancient times for its use in preparing an extract, which upon drinking, is reported to reduce fatigue and produce complete freedom from anxiety (1).
"The National Standard Dispensatory" of 1909 (2) describes P. methysticurm and lists as a pharmaceutical preparation fluid extract of kava N.F. The same edition has a long list on action and uses of the drug. Marpmann demonstrated in 1905 (3) that the constituent kawain possesses bacteriological properties, espeaally for the gonococcus, but also for the Coli bacillus.
The remarkable physiological action of P . metkysticum has prompted numerous chemical investigations, dating from an article by Gobley in 1860 (4). The most extensive work on the constituents of this plant was carried out by W. Borsche and his co-workers, who in a series of 14 papers extending over a period of 19 years (1914-1933) reported the isolation and structure of two new compounds, kawain (Gonosan) and dihydrokawain (DHK). These workers also elucidated the structures of other crystalline components, methysticin, dihydromethysticin (DHM), and yangonin, which had previously been isolated from this plant. At the conclusion of his work, Borsche stated that all of these compounds failed to exhibit the typical