587-63-3

Usage

Uses

Used in Herbal Medicine:
DIHYDROKAVAIN is used as a therapeutic agent for treating sleep disturbances, stress, and anxiety. Its anxiolytic effects have been observed in studies, such as one conducted on chicks, which suggests that it contributes significantly to the overall calming properties of kava.
Used in the Beverage Industry:
DIHYDROKAVAIN is used as an active ingredient in kava beverages, which are consumed by South Pacific islanders. These beverages are known for their relaxing and stress-relieving properties, making them a popular choice for social and ceremonial occasions.
Used in Pharmaceutical Research:
Due to its potential anxiolytic effects, DIHYDROKAVAIN is also used as a subject of research in the pharmaceutical industry. Scientists are exploring its potential applications in the development of new drugs and therapies for anxiety and stress-related disorders.
Used in Dietary Supplements:
DIHYDROKAVAIN is used as an ingredient in dietary supplements that aim to promote relaxation, reduce stress, and improve sleep quality. These supplements are often marketed to individuals seeking natural alternatives to conventional medications for anxiety and sleep disorders.

Preparation

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

InChI:InChI=1/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3/t12-/m0/s1

Upstream product

• 500-64-1 kawain 
• 77-78-1 dimethyl sulfate 
• 182950-96-5 (6S)-6-(2-phenylethyl)dihydropyran-2,4⁽³⁾-dione 
• 1952-41-6 5,6-dehydrokawain 
• 104-53-0 3-phenyl-propionaldehyde 
• 90857-62-8 Brassard's diene 
• 30414-58-5 methyl 3-oxo-5-phenylpentanoate 
• 100-39-0 benzyl bromide 
• 182950-95-4 (S)-5-hydroxy-3-oxo-7-phenyl-heptanoic acid tert-butyl ester 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 
• 592533-53-4 C₁₃H₁₄O₃ 
• 1443322-44-8 methyl 3-[(2S)-2-hydroxy-4-phenylbutyl]but-3-enoate 
• 913258-21-6 (4S)-4-(2-phenylethyl)-1,3,2-dioxathiolane 2-oxide 

Downstream Products

• 845533-34-8 (8S)-hydroxy-(6S)-dihydrokawain 

Relevant academic research and scientific papers

Asymmetric synthesis of (S)-dihydrokavain from l-malic acid

A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination.

Enantioselective synthesis of (+)-(S)-7,8-dihydrokavain and (4R,6R)-4-hydroxy-6-(2-phenylethyl)tetrahydro-2H-pyran-2-one, lactone analog of compactin and mevinolin

A simple and efficient asymmetric synthesis was performed of (+)-(S)-7,8-dihydrokanian and (4R,6R)-4-hydroxy-6-(2-phenylethyl)tetrahydro-2H- pyran-2-one involving Keck allylation in the key stage of building up the carbon scaffold of the target molecules.

Efficient enantioselective hetero-diels-alder reaction of brassard's diene with aliphatic aldehydes: A one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain

An efficient catalytic asymmetric hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes was reported The catalyst which was generated from (R)-BINOL, Ti(i-PrO)4, and 4-picolyl chloride hydrochloride, promoted the reaction smoothly to afford the corresponding α, β-unsaturated λ-lactone derivatives in moderate-to-good yields (46-79%) with high enantioselectivities (up to 88% ee) Natural products (R)-(+)-kavain (70% ee, > 99% ee after single re crystallization) and (S)-(+)-dihydrokavain (84% ee) were also prepared in one step by using this methodology.

Asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain via cobalt catalyzed hydrolytic kinetic resolution of epoxides

A concise route to the asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain has been described using Co-catalyzed hydrolytic kinetic resolution of racemic epoxides and regiospecific opening of terminal epoxides with dimethylsulfonium me

Chemoenzymatic synthesis of enantiomerically enriched kavalactones

Lipase-mediated kinetic resolution of methyl-3-hydroxy-5-phenylpentanoate and (6E)-ethyl 5-hydroxy-3-oxo-7-phenylhept-6-enoate is described in high enantiomeric excess and good yields. The effect of different lipases in different solvents has been screened using different acylating agents. This protocol has been extended for the preparation of enantiomerically pure biologically important kavalactones.

Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain

An efficient and versatile synthetic method has been developed and utilized for the stereoselective synthesis of (R)-(+)-goniothalamin 1, (R)-(+)-kavain 2 and (S)-(+)-7,8-dihydrokavain 3. Application of the Cosford protocol and direct conversion of aldehydes to β-keto-esters are the key steps in our approach.

A total synthesis of (+)- and (-)-dihydrokavain with a sonochemical blaise reaction as the key step

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)-(

Enantioselective catalysis of the hetero-diels-alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: A one-step synthesis of (S)-(+)-dihydrokawain

The first catalytic enantioselective hetero-Diels-Alder reaction between Brassard's diene and aldehydes has been achieved through hydrogen-bonding activation using TADDOL derivatives as catalysts to afford the corresponding δ-lactone derivatives in modera

Asymmetric synthesis of kavalactones

This invention relates to preparation of enantio-enriched compounds, and more particularly to enantio-enriched kavalactone compounds and derivatives thereof. The methods provide compounds that are useful as reagents, or building blocks, in the constructio

Heterogeneous enantioselective hydrogenation of 2-pyrones over cinchona-modified palladium

Asymmetric hydrogenation of 4-alkoxy and 4-methyl derivatives of 2-pyrones to the corresponding dihydro- or tetrahydropyrones over cinchona-modified Pd/TiO2 is fast under ambient conditions and affords good yields and high ee. cis-Tetrahydropyr