132971-59-6Relevant articles and documents
A facile synthesis of cytogenin (8-hydroxy-3-hydroxymethyl-6- methoxyisocoumarin)
Saeed, Aamer
, p. 975 - 978 (2004)
A facile and straightforward synthesis of cytogenin 1 (8-hydroxy-3- hydroxymethyl-6-methoxyisocoumarin) metabolite of Streptoverticillium eurocidicum and Certocystis fimbriata has been achieved. Condensation of chloroacetyl chloride with 3,5-dimethoxyhomophthalic acid 2 directly furnished 3-chloromethyl-6,8-dimethoxyisocoumarin 3 which was hydrolyzed to 6,8-dimethoxy-3-hydroxymethylisocoumarin 4 using 0.05% aqueous sodium hydroxide in THE Regioselective demethylation of 4 yielded cytogenin 1. In model experiments, 3-chloromethylisocoumarin was prepared and converted into 3-hydroxymethyl isocoumarin.
Bioactive compounds from the scale insect fungus Conoideocrella tenuis BCC 44534
Saepua, Siriporn,Kornsakulkarn, Jittra,Somyong, Wiwat,Laksanacharoen, Pattiyaa,Isaka, Masahiko,Thongpanchang, Chawanee
, p. 859 - 866 (2018/01/17)
Eleven new compounds, including two quinone derivatives of bioxanthracene, conoideocrellones A (1) and B (2), two bioxanthracenes 3 and 4, four isocoumarins and isocoumarin glycosides 7–10, two phenolic compounds 16 and 17, and a diterpenoid compound, conoideocin A (18), were isolated from culture of the scale-insect pathogenic fungus Conoideocrella tenuis BCC 44534. Seventeen known compounds, compounds 5 and 6, ES-242-2 and its atropisomer, isocoumarins and isocoumarin glycosides 11–15, 3,4,6-trihydroxymellein, cis-4,6-dihydroxymellein, metarhizins A (19) and B (20), BR-050 (21), 5α,8α-epidioxy-24(R)-methylcholesta-6,22-dien-3β-ol, zeorin, and conoideocrellide A, were also isolated from this fungus. Structures of these compounds were elucidated by NMR and MS data analyses. Compound 4 was active against Plasmodium falciparum K1 (IC50 6.6 μg/mL), while it did not show cytotoxicity. Conoideocrellone A (1) and compounds 3 and 7 exhibited cytotoxic activity, while conoideocin A (18) showed broad range of biological activities including antimalarial, antibacterial, and cytotoxic activities.
Gold(I)-Catalyzed Cyclization for the Synthesis of 8-Hydroxy-3- substituted Isocoumarins: Total Synthesis of Exserolide F
Mallampudi, N. Arjunreddy,Reddy, G. Sudhakar,Maity, Saurabh,Mohapatra, Debendra K.
, p. 2074 - 2077 (2017/04/28)
A highly regioselective gold(I)-catalyzed 6-endo-dig cyclization of 2,2-dimethyl-5-(alkynyl)-4H-benzo[d][1,3]dioxin-4-ones for the synthesis of 8-hydroxy-3-substituted isocoumarins is described. Key features of the reaction include the broad substrate scope, scalability, and tolerance for protecting groups. The synthetic utility of this novel method is demonstrated by the first total synthesis of exserolide F, an isocoumarin-containing polyol natural product.
A simple and efficient synthesis of isocoumarins and alkylidenephthalides from 3-(1-hydroxycarbethoxy/alkyl)phthalides with a DEAD/PPh3/TBHP system
Gadakh, Sunita K.,Sudalai, Arumugam
, p. 57658 - 57661 (2015/02/19)
A facile and novel approach to the synthesis of 3-carbethoxy-isocoumarins and 3-alkylidenephthalides is described. The methodology employs DEAD/PPh3/TBHP as the reagent system proceeding through unprecedented 1,2-shift intramolecular ring expansion or simple elimination depending upon substituents present on 3-substituted phthalides, with broader substrate scope. This strategy is amply demonstrated in the short synthesis of bioactive molecules such as cytogenin and (Z)-3-butylidene-7-hydroxy-5-methoxyphthalide. This journal is
