116349-04-3Relevant academic research and scientific papers
Chemoenzymatic Synthesis of Methyl (6S)-(-)-6,8-Dihydroxyoctanoate: A Precursor to (R)-(+)-α-Lipoic Acid
Laxmi, Y. R. Santosh,Iyengar, D. S.
, p. 594 - 596 (1996)
A short synthetic sequence for the preparation of methyl (6S)-(-)-6,8-dihydroxyoctanoate, the precursor to (R)-(+)-α-lipoic acid is described starting from (2S)-(+)-2-(tetrahydro-2-furyl)ethanol.
A Novel Enantiospecific Synthesis of (S)-(-)-Methyl 6,8-Dihydroxyoctanoate, a Precursor of (R)-(+)-α-Lipoic Acid
Dasaradhi, L.,Fadnavis, N. W.,Bhalerao, U. T.
, p. 729 - 730 (1990)
(S)-(-)-Methyl 6,8-dihydroxyoctanoate has been synthesised, with stereocontrolled reduction of methyl 8,8-dimethyl-6-oxo-octanoate using immobilised Bakers yeast as a key step.
A short enantioselective formal synthesis of methyl (S)-(-)-6,8-dihydroxyoctanoate: A key intermediate for the synthesis of R-(+)-α-lipoic acid
Bezbarua, Maitreyee,Saikia, Anil K.,Barua, Nabin C.,Kalita, Dipak,Ghosh, Anil C.
, p. 1289 - 1290 (1996)
A short enantioselective formal synthesis of methyl (S)-(-)-6,8-dihydroxyoctanoate starting from readily available 2-nitrocyclohexanone using a novel retro-Henry reaction is described.
Chirality induction and chiron approaches to enantioselective total synthesis of α-lipoic acid
Chavan, Subhash P.,Pawar, Kailash P.,Praveen, Ch.,Patil, Niteen B.
, p. 4213 - 4218 (2015/06/02)
Abstract An efficient, short and convenient asymmetric synthesis of (R)-(+)-lipoic acid in seven steps from chiral hydroxy aldehyde with 32.5% overall yield is described. Synthesis of S and R enantiomers of α-lipoic acid from cis-1,4-butene diol derived chiral lactone is reported with 34 % overall yield. The present synthesis involves use of simple reaction conditions making it a convenient synthesis.
An enantioselective formal synthesis of (+)-(R)-α-lipoic acid by an L-proline-catalyzed aldol reaction
Zhang, Shilei,Chen, Xiaobei,Zhang, Jiangang,Wang, Wei,Duan, Wenhu
, p. 383 - 386 (2008/09/20)
An efficient, highly stereocontrolled formal synthesis of (+)-(R)-α-lipoic acid was achieved, which utilizes an L-proline-catalyzed highly enantio- and diastereoselective cross-aldol reaction as the key step. Georg Thieme Verlag Stuttgart.
An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution
Bose, D. Subhas,Fatima, Liyakat,Rajender, Salla
, p. 1863 - 1867 (2008/01/27)
A general and practical approach for the synthesis of C-4 chiral building blocks using Jacobsen's hydrolytic kinetic resolution technique to resolve terminal epoxides and diols in high enantiomeric excess and excellent yields is described. The utilization of these building blocks for the synthesis of biologically important natural products L-carnitine and α-lipoic acid is illustrated. Georg Thieme Verlag Stuttgart.
Method for producing enantiomer-free 6,8 dihydroxy octanoic acid esters by means of asymmetric, catalytic hydrogenation
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, (2008/06/13)
The invention relates to a process for the preparation of compounds of the general formula I in which R1 represents a C1-C20-alkyl group, a C3-C12-cycloalkyl group, a C7-C12-aralkyl group or a mono- or bi-nuclear aryl group, in which a ketone of formula II wherein R1 is as defined above, is subjected to asymmetric hydrogenation.
Preparation of dihydroxycarboxylic esters in the absence of solvents
-
, (2008/06/13)
A description is given of a process for preparing dihydroxycarboxylic esters and of an overall process for preparing R-(+)-α-lipoic acid.
Asymmetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-α-lipoic acid
Upadhya,Nikalje,Sudalai
, p. 4891 - 4893 (2007/10/03)
The asymmetric synthesis of methyl (S)-6,8-dihydroxyoctanoate (5) and (S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid (13), key precursors to R-(+)-α-lipoic acid (6) is described using OsO4-catalyzed asymmetric dihydroxylation and Ru-catalyzed asymmetric hydrogenation, respectively, as the key steps in the reaction sequence. These methods lead to an efficient formal synthesis of R-(+)-α-lipoic acid in 90% ee.
A short and productive synthesis of (R)-α-Lipoic acid
Bringmann, Gerhard,Herzberg, Daniela,Adam, Geo,Balkenhohl, Friedhelm,Paust, Joachim
, p. 655 - 661 (2007/10/03)
(R)-α-Lipoic acid is synthesized in seven steps from the base chemicals methyl acetoacetate or Meldrum's acid and monomethyl adipate. The key steps are the introduction of the stereogenic center by fermentative or homogeneously catalyzed hydrogenation of 3-oxooctanedioic acid diester to (3S)-3-hydroxyoctanedioic acid diester and its regioselective reduction to (6S)-6,8-dihydroxyoctanoic acid ester. The overall yield of (R)-α-lipoic acid, starting from 3-oxooctanedioic acid diester, is 40%.
