Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods

2007-03-01
Demir, Ayhan Sıtkı
Caliskan, Zerrin
Sahin, Ertan
The chemoenzymatic synthesis of both of the enantiomers of pharmacologically interesting compounds such as 4,5,6,7-tetrahydro-4-oxobenzofuran-5-yl acetate (2a), 4,5,6,7-tetrahydro-4-oxo-6,6-dimethylbenzofuran-5-yl acetate (2b), and their hydroxy derivatives 3a, 3b, 1-benzyl4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate (5), starting from 6,7-dihydrobenzofuran-4(5H)-one (la), 6,7-dihydro-6,6-dimethylbenzofuran4(5H)-one (7b), and 1-benzyl-6,7-dihydro-1 H-indol-4(5H)-one (4) are reported. Manganese(III) acetate-mediated acetoxylation followed by the enzyme-mediated kinetic resolution of alpha'-acetoxy enone provides acetoxy and hydroxy derivatives in good yields and high enantiomeric excesses.
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

Suggestions

Immobilization of dioxomolybdenum(VI) complex bearing salicylidene 2-picoloyl hydrazone on chloropropyl functionalized SBA-15: A highly active, selective and reusable catalyst in olefin epoxidation
Bagherzadeh, Mojtaba; Zare, Maryam; Salemnoush, Taghi; Özkar, Saim; Akbayrak, Serdar (Elsevier BV, 2014-04-05)
A novel organic-inorganic hybrid heterogeneous catalyst system was obtained from the reaction of the molybdenum(VI) complex of salicylidene 2-picoloyl hydrazone with mesoporous silica containing 3-chloropropyl groups prepared by a direct synthetic approach involving hydrolysis and co-condensation of tetraethylorthosilicate (TEOS) and 3-chloropropyltrimethoxysilane in the presence of the triblock copolymer P123 as template under acidic conditions. Characterization of the functionalized materials by X-ray dif...
Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl)ethan-1-ol as a flexible building block for the preparation of serine and azasugars
Demir, Ayhan Sıtkı; Sesenoglu, O; Aksoy-Cam, H; Kaya, H; Aydogan, K (Elsevier BV, 2003-05-16)
The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)- and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl)ethan-1-ol with an ee of up to 96%.
L-Dopa synthesis using tyrosinase immobilized on magnetic beads
Tuncagil, Sevinc; Kayahan, Senem; BAYRAMOĞLU, GÜLAY; ARICA, MEHMET YAKUP; Toppare, Levent Kamil (Elsevier BV, 2009-06-01)
Magnetic beads were prepared via Suspension polymerization of glycidyl methacrylate (GMA) and methyl methacrylate (MMA) in the presence of ferric ions. Following polymerization, thermal co-precipitation of the Fe(III) ions in the beads with Fe(II) ions under alkaline condition resulted in encapsulation of Fe3O4 nano-crystals within the polymer matrix. The magnetic beads were activated with glutaraldehyde, and tyrosinase enzyme was covalently immobilized on the support via reaction of amino groups under mild...
Palladium doped perovskite-based NO oxidation catalysts: The role of Pd and B-sites for NOx adsorption behavior via in-situ spectroscopy
Say, Zafer; Dogac, Merve; Vovk, Evgeny I.; Kalay, Yunus Eren; KIM, Chang Hwan; LI, Wei; Ozensoy, Emrah (Elsevier BV, 2014-07-01)
Perovskite-based materials (LaMnO3, Pd/LaMnO3, LaCoO3 and Pd/LaCoO3) were synthesized, characterized (via BET, XRD, Raman spectroscopy, XPS and TEM) and their NO (x= 1,2) adsorption characteristics were investigated (via in-situ FTIR and TPD) as a function of the nature of the B-site cation (i.e. Mn vs Co), Pd/PdO incorporation and H-2-pretreatment. NO adsorption on of LaMnO3 was found to be significantly higher than LaCoO3, in line with the higher SSA of LaMnO3. Incorporation of PdO nanoparticles with an a...
Aryl butenoic acid derivatives as a new class of histone deacetylase inhibitors: synthesis, in vitro evaluation, and molecular docking studies
Esiyok, Peruze Ayhan; Seven, Ozlem; Eymur, Guluzar; Tatar, Gamze Bora; DAYANGAÇ ERDEN, DİDEM; YELEKÇİ, Kemal; YURTER, HAYAT; Demir, Ayhan Sıtkı (The Scientific and Technological Research Council of Turkey, 2014-01-01)
New aryl butenoic acid derivatives have been synthesized by combining hydroxy- or methoxy-substituted phenyl rings as the capping group, with a double bond in the short linker as well as metal binding groups, enoic ester, and salts bearing either methyl or morpholine. These compounds have been shown to possess promising histone deacetylase inhibition activities via in vitro fluorometric assay and molecular docking studies.
Citation Formats
A. S. Demir, Z. Caliskan, and E. Sahin, “Enantioselective synthesis of 4,5,6,7-tetrahydro-4-oxo-benzofuran-5-yl acetate and 1-benzyl-4,5,6,7-tetrahydro-4-oxo-1(H)-indol-5-yl acetate using chemoenzymatic methods,” JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, pp. 87–92, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56394.