147666-84-0Relevant articles and documents
Thunberginols A, B, and F, new antiallergic and antimicrobial principles from hydrangeae dulcis folium.
Yoshikawa,Uchida,Chatani,Murakami,Yamahara
, p. 3121 - 3123 (1992)
Six new antiallergic and antimicrobial principles, thunberginols A, B, C, D, E, and F, were isolated from Hydrangeae Dulcis Folium, the fermented and dried leaves of Hydrangea macrophylla SERINGE var. thunbergii MAKINO. The chemical structures of thunberginols A, B, and F have been determined on the basis of chemical and physiocochemical evidence. Thunberginols A, B, and F showed more potent antiallergic activity than phyllodulcin, hydrangenol, and AA-861 in the in vitro test using the Schults-Dale reaction in sensitized guinea pig bronchial muscle. Thunberginols A, B, and F also exhibited antimicrobial activity against oral bacteria.
Reaction of arynes with trifluoroacetylated β-diketones: Novel formation of isocoumarins and phenanthrenes
Okuma, Kentaro,Tanabe, Yukiko,Fukami, Takuto,Ishibashi, Yuto
, (2018/11/10)
Polysubstituted isocoumarins were synthesized by the reaction of substituted 2-(trimethylsilyl)aryl triflates with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded through carbon-carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β-diketones to afford phenanthrenes and 1,2-diarylethanones. Although reaction of 2-(trimethylsilyl)phenyl triflate with 1,1,1-trifluoro-4′-methylbenzoylacetone in the presence of CsF gave 3-(4′-methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9-(4-methylbenzoyl)-10-trifluoromethylphenanthrene in 35% yield.
Palladium-catalyzed aryl halide carbonylation-intramolecular O-enolate acylation: Efficient isocoumarin synthesis, including the synthesis of thunberginol A
Tadd, Andrew C.,Fielding, Mark R.,Willis, Michael C.
supporting information; experimental part, p. 6744 - 6746 (2010/03/25)
Exposure of a series of a-(o-haloaryl)-substituted ketones to palladium-catalyzed carbonylation conditions leads to the formation of the corresponding isocoumarins. Balloon pressure of CO is sufficient to achieve high yielding reactions, and both cyclic a
Synthesis of 3-arylisocoumarins, including thunberginols A and B, unsymmetrical 3,4-disubstituted isocoumarins, and 3-ylidenephthalides via iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids
Rossi, Renzo,Carpita, Adriano,Bellina, Fabio,Stabile, Paolo,Mannina, Luisa
, p. 2067 - 2081 (2007/10/03)
3-Aryl-4-iodoisocoumarins, which were readily and efficiently prepared by regioselective iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids, were used as precursors either to 3-arylisocoumarins, including naturally-occurring