73536-68-2

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 104-53-0 3-phenyl-propionaldehyde 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 36185-09-8 1-phenylhex-5-yn-3-ol 
• 104-55-2 3-phenyl-propenal 
• 500-64-1 kawain 
• 99902-35-9 5-phenylpent-1-yn-3-ol 
• 77-78-1 dimethyl sulfate 
• 195376-03-5 6-(2-hydroxy-4-phenylbutyl)-2,2-dimethyl-4H-1,3-dioxin-4-one 

Relevant academic research and scientific papers

Pilot in Vivo Structure-Activity Relationship of Dihydromethysticin in Blocking 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-Induced O6-Methylguanine and Lung Tumor in A/J Mice

(+)-Dihydromethysticin was recently identified as a promising lung cancer chemopreventive agent, while (+)-dihydrokavain was completely ineffective. A pilot in vivo structure-activity relationship (SAR) was explored, evaluating the efficacy of its analogs in blocking 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced short-term O6-methylguanine and long-term adenoma formation in the lung tissues in A/J mice. Both results revealed cohesive SARs, demonstrating that the methylenedioxy functional group in DHM is essential while the lactone functional group tolerates modifications.

Lewis base-catalyzed divergent isomerizations of 5-hydroxyl-2,3-dienoate

A divergent isomerization of 5-hydroxyl-2,3-dienoate 1 catalyzed by Lewis base has been developed, the phosphine catalyst leads to 5-oxohex-2(3)-enoates 2 while DABCO catalyst affords 3-ethoxy α,β-unsaturated lactone 3.

Synthesis of β-methoxyacrylate natural products based on box-Pd IIcatalyzed intermolecular methoxycarbonylation of alkynoles

Bis(oxazoline)-palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6-membered lactone 3a-k in good combined yield. In the case of propargyl alcohols, 5-membered lactones 3p, 3q, 16 were obtained in moderate yields. The one-pot synthesis of kawa lactones 3a, 3r, 3s and formal synthesis of dihydroxycystothiazole A and dihydroxycystothiazole C are presented. To elucidate the stereochemistry of (+)-annularin G and (-)-annularin H, the first asymmetric syntheses of these natural products were achieved.

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.

Versatile asymmetric synthesis of the kavalactones: First synthesis of (+)-kavain

(Equation Presented) Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.

Polymer-supported electron-rich diene for hetero Diels-Alder reactions

A Brassard diene analogue was grafted on a modified Merrifield resin and used in a hetero Diels-Alder reaction with various aldehydes or ketones. The reaction gave access to 6-substituted 5,6-dihydropyrones (5a-u). This new immobilized electron-rich diene is more stable than the corresponding native diene, and is a versatile supported reagent.

Wood preservative

A wood preservative that comprises as an active ingredient a Piper methysticum, plant or a processed product thereof or a compound represented by Formula (I): wherein R1, R2, R3, R4 and R16 are same or different and each denotes a hydrogen atom, hydroxy or a C1-4 alkoxy, or R1 and R2 are taken together to form a group represented by —O—(CH2)n—O— wherein n is an integer of 1 to 3, R5 is a C1-4 alkoxy and X is —CH=CH—, —CH2—CH2— or epoxyethylene, and the bond: denotes a single bond or a double bond can prevent the attacking wood by an insect harmful to the wood and also prevents the appearance and the growth of a wood-rotting fungus or a wood- staining fungus while being highly safe to humans and animals without exerting no adverse effect on the environment.