587-63-3

White-pale yellow powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from the rhizome of kava-kava (Piper methysticum G. Forst).

(+)-(S)-Dihydrokavain is a kavalactone found in kava beverages consumed by South Pacific islanders. Furthermore, roots and extracts of the kava plant have been used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.

Dihydrokavain is one of the six major kavalactones found in the kava plant; appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.Used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.

ChEBI: Dihydrokavain is a member of 2-pyranones and an aromatic ether.

Starting from 2,3-O-isopropylidene-D-glyceraldehyde (2) as chiral material, the naturally occurring (S)-(+)-dihydrokavain (1a) was synthesized by a procedure that involves a sonochemical Blaise reaction as the key step. The absolute configuration of (S)-(+)-dihydrokavain (1a) is demonstrated for the first time by total synthesis from a chiral source. Its opposite enantiomer, (R)-(–)-dihydrokavain (1b), was also synthesized after inversion of the chiral center in a Mitsunobu reaction.
A Total Synthesis of (+)- and (–)-Dihydrokavain with a Sonochemical Blaise Reaction as the Key Step