专利号:US-2011245503-A1 优先权日:2008-11-28 标题 :Enantioselective synthesis of asymmetric beta-carboline intermediates 发明人:SANTOS LEONARDO; ESPINOZA MORAGA MARLENE; SHANKARAJAH NAGULA 权利人:UNIV TALCA 摘要:Described herein is a new asymmetric synthesis of imines to obtain β-carboline derivatives useful as key intermediate compounds for the synthesis of phosphodiesterase inhibitors using a new process with palladium or ruthenium hydride and/or nickel boride to reduce chiral intermediates. The use of chloroformate chiral auxiliaries is further described for the reduction and asymmetric hydrogenation of imines to obtain β-carboline derivatives and intermediate compounds used in the preparation thereof.
专利号:US-4985567-A 优先权日:1988-03-07 标题:Chiral phosphinopyrrolidine compounds and their use for asymmetric synthesis of optically active compounds 发明人:ACHIWA KAZUO; TAKEDA HIDEO 权利人:KAZUO ACHIWA; FUJI YAKUHIN KOGYO KK 摘要:New chiral phosphinopyrrolidine compounds of the general formula: ##STR1## wherein R 1 is hydrogen or --COA 1 , --COOA 2 , --CONHA 3 , --SO 2 A 4 or --PO(A 5 ) 2 , A 1 , A 2 , A 3 , A 4 and A 5 each represents independently alkyl or aryl, R 2 is phenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, and R 3 is phenyl, lower-alkylphenyl, di(lower-alkyl)aminophenyl, lower-alkoxyphenyl or 3,5-dimethyl-4-methoxyphenyl, with the proviso that R 2 and R 3 may not simultaneously by phenyl, p-di(lower-alkyl)-aminophenyl or p-lower-alkoxyphenyl, as well as the use of these compounds as ligand for a metal complex catalyst for asymmetric synthesis of optically active compounds. The new chiral phosphinopyrrolidine compounds are useful ligands which attain both of high optical yield and high reaction efficiency in catalytic asymmetric reduction.
专利号:US-2007015798-A1 优先权日:2005-02-25 标 题 :Efficient and stereoselective process for large scale synthesis of (3R)-3-(2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydropyrrolo[3,4-b]quinolin-9-one derivatives 发明人:LI XUN; LEMAIRE SEBASTIEN; MARKO ISTVAN; WILLEMSENS ALBERT 权利人:LI XUN; LEMAIRE SEBASTIEN; MARKO ISTVAN; WILLEMSENS ALBERT 摘要:This invention relates to an efficient process for large scale stereoselective production of (3R)-3-(2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydropyrrolo[3,4-b]quinolin-9-ones and key intermediates used for the preparation of benzofuranyl pyrroloquinolones as potent and selective PDE5 inhibitors for the treatment of erectile dysfunction, as well as pharmaceutical compositions and methods of treatment utilizing these compounds.
专利号:EP-1851227-A1 优先权日:2005-02-25 标题 :An efficient and stereoselective process for large scale synthesis of 3-(r)-3- (2,3-dihydrobenzofuran-5-yl)-1,2,3,4- tetrahydropyrrolo{3,4-b}quinolin-9-one
专利号:CN-111440121-A 优先权日:2020-03-26 标 题 :A method for the separation of two key intermediates in the total synthesis of optically pure tetrandrine
专利号:CN-111440121-B 优先权日:2020-03-26 标 题 :A method for splitting two key intermediates in the total synthesis of optically pure tetrandrine
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合成参考文献
参考文献:10.1016/j.jmb.2004.07.023|10.2210/pdb1xpy/pdb|10.2210/pdb1xs2/pdb 摘要:Wang WC, Chiu WC, Hsu SK, Wu CL, Chen CY, Liu JS, Hsu WH. Structural basis for catalytic racemization and substrate specificity of an N-acylamino acid racemase homologue from Deinococcus radiodurans. J Mol Biol. 2004 Sep 03;342(1):155–69. doi: 10.1016/j.jmb.2004.07.023.