104265-88-5Relevant academic research and scientific papers
A Study of Stereoselective Hydrolysis of Symmetrical Diesters with Pig Liver Esterase
Mohr, Peter,Waespe-Sarcevic, Nada,Tamm, Christoph,Gawronska, Krystyna,Gawronsky, Jacek K.
, p. 2501 - 2511 (1983)
Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl esters of symmetrical dicarboxylic acids, including meso-diacids, cis-1,2-cycloalkanedicarboxylic acids, and diacids with a prochiral center, was studied with 14 substrates.The products of these stereoselective hydrolyses are chiral monoesters of dicarboxylic acids, with an enantiomeric excess (e.e.) from 10percent to 100percent.Some of these optically active monoesters are valuable synthons in natural products synthesis.An additivity pattern of α- and β-substituents with the glutaric esters on the stereoselectivity of enzymatic hydrolysis was observed.Analysis of the experimental results leads to a model of enzyme stereoselectivity of diester hydrolysis in which the substitution pattern at α- and β-C-atoms is found to determine the absolute configuration of the resulting monoester.
Enzyme-catalysed Asymmetric Synthesis, IV. - Synthesis of Homochiral Building Blocks for the Enantioselective Total Synthesis of Cyclopentanoids with an Esterase-catalysed Asymmetric Reaction as Key Step
Gais, Hans-Joachim,Lukas, Karl L.,Ball, Walter A.,Braun, Siegmar,Lindner, Hans J.
, p. 687 - 716 (2007/10/02)
An efficient synthesis of the homochiral building blocks 2a and ent-2a based on the "enantiotopos-enzyme concept" for the total synthesis of cyclopentanoids is described.Key steps thereof are the almost quantitative PLE-catalysed asymmetric hydrolysis of the meso-diester 8 to the homochiral hemiester 9, whose absolute configuration was determined by crystal structure analysis of the (-)-ephedrine salt 12, the preparation of optically pure 9 and ent-9 by a racemate resolution of rac-9 using (+)- and (-)-ephedrine, the enantiodivergent synthesis of the lactones 18 and ent-18 from 9, as well as the enantioconvergent synthesis of 18 or ent-18 from 9 and ent-9 by optional chemoselective reduction of the ester and carboxy group, and finally the regioselective Dieckmann cyclisation of the isomeric diesters 23b/24b and ent-23b/ent-24b, respectively, to give the cyclopentanoid target compounds 2a and ent-2a.The structures of 23b, 24b, rac-2b, and rac-29 were determined by INADEQUATE-13C-NMR experiments.Dieckmann cyclisation of the trans-diester rac-31 also leads to rac-2a and rac-26a.
SYNTHESIS OF THROMBOXANE A2 ANALOGS-2. (+/-)-THIATHROMBOXANE A2
Ohuchida, Shuichi,Hamanaka, Nobuyuki,Hayashi, Masaki
, p. 4263 - 4268 (2007/10/02)
The total synthesis of (+/-)-11a-methano-9,11-thiathromboxane A2(1), the sulfur analog of thromboxane A2 is described.
