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A Short and Productive Synthesis of (R)-α-Lipoic Acid

  • Gerhard Bringmann , Daniela Herzberg , Geo Adam , Friedhelm Balkenhohl and Joachim Paust
Published/Copyright: June 2, 2014
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 54 Issue 5

(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%.

Keywords : Lipoic Acid; Yeast Reduction; Enantioselective Hydrogenation; Regioselective Reduction
Received: 1999-12-4
Published Online: 2014-6-2
Published in Print: 1999-5-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

Articles in the same Issue

  1. Chemische Reaktionen in Salzschmelzen, XXI. Titan-vermittelte Synthese von Silanen in Chloroaluminat-Schmelzen / Chemical Reactions in Molten Salts, XXI. Titanium Mediated Synthesis of Silanes in Chloroaluminate Melts
  2. Hydrolytische Bildung von Perchlorsiloxanen / Formation of Chlorosiloxanes by Hydrolysis
  3. Umsetzung von Cyclopentadienylmetallcarbonylen mit Thionylhalogeniden - Neue Synthese halogenoverbrückter Cp*Co-Komplexe / Reaction of Cyclopentadienyl Metal Carbonyles with Thionylhalides - New Synthesis of Halogeno-Bridged Cp*Co Complexes
  4. Die Oxochlorovanadate PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN und (PPh4)2[VOCl4]·CH3CN mit auffälligen Abweichungen von der quadratisch-pyramidalen Anionenstruktur / The Oxochlorovanadates PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN and (PPh4)2[VOCl4]·CH3CN with Remarkable Deviations from the Square-Pyramidal Anion Structure
  5. S-, X-, Q- und W-Band-Pulver-EPR-Untersuchungen an Tetra-n -butylammonium-bis( 1,2-dicyanoethen-1,2-dithiolato)aurat(II), [(n-C4H9)4N]2[AuII(mnt)2] / S, X, Q and W Band Powder-EPR Investigations on Tetra-n-butylammoniumbis( 1,2-dicyanoethylene-1,2-dithiolato)aurate(II), [(n-C4H9)4N]2 [AuII(mnt)2]
  6. Unerwartete Reaktionsprodukte bei der Umsetzung von Mesitylmagnesiumbromid mit Arsentribromid / Unexpected Products from the Reaction of Mesitylmagnesium Bromide and Arsenic Tribromide
  7. 1.3.5-Triazin-2,4,6-trisulfenyltrichlorid: Synthese, Eigenschaften und Reaktionsverhalten / 1.3.5-Triazine-2,4,6-trisulfenyltrichloride: Synthesis, Properties and Reactions
  8. Verdampfungsverhalten von Lanthantrihalogeniden / Evaporation Behaviour of Lanthanum Trihalides
  9. Synthese und Molekülstruktur des [α-(Dichlormethylsilyl)ethyl]- dichlorboran-dimethylsulfid / Synthesis and Molecular Structure of [α-(Dichloromethylsilyl)ethyl]- dichloroborane-dimethylsulfide
  10. Organogallitimamide: Synthese und Kristallstrukturen von [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2 / Organogallium Amides: Synthesis and Crystal Structures of [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2
  11. α-Dicarbonylmonoxime als Nucleophile und Nachbargruppen / α-Dicarbonylmonoximes as Nucleophiles and Neighbour Groups
  12. Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides
  13. A Short and Productive Synthesis of Racemic α-Lipoic Acid
  14. A Short and Productive Synthesis of (R)-α-Lipoic Acid
  15. 5,10,15,20-Tetrakis(diphenylmethyl)porphyrin - A Nonplanar Porphyrin with Intermediate Degree of Ruffling
  16. Synthesis of 3-Amino(alkoxy)-2,4-dioxo-1,3-oxazolidine-5-carboxylates from Tartronic Esters
  17. Cyanothioacetamide and its Derivatives in Heterocyclic Synthesis: A New Route for the Synthesis of Several Pyridine and Thieno[2,3-b]pyridine Derivatives and their Biological Evaluation
  18. Synthese und Struktur von Prolinring-modifizierten Actinomycinen des X-Typs / Synthesis and Structure of Proline Ring Modified Actinomycins of the X-Type
  19. Neighbouring Group Participation of C-6 Substituents of Glucose Derivatives on the Stereoselectivity of the N-Glycosidic Linkage of Glycopeptides
  20. Synthese und Kristallstruktur von 3.6-Di-tert-butylpyridazin / Synthesis and Crystal Structure of 3.6-Di-tert-butylpyridazine
  21. p-Tolyl(trimethylsilylethynyl)sulfone as Synthon for the Synthesis of Cp(OC)2M-C =CSiMe3 (M ≡ Fe, Ru). Molecular Structure of Cp(OC)2Fe-C ≡ CSiMe3
https://doi.org/10.1515/znb-1999-0514
Keywords for this article
Lipoic Acid; Yeast Reduction; Enantioselective Hydrogenation; Regioselective Reduction

Articles in the same Issue

  1. Chemische Reaktionen in Salzschmelzen, XXI. Titan-vermittelte Synthese von Silanen in Chloroaluminat-Schmelzen / Chemical Reactions in Molten Salts, XXI. Titanium Mediated Synthesis of Silanes in Chloroaluminate Melts
  2. Hydrolytische Bildung von Perchlorsiloxanen / Formation of Chlorosiloxanes by Hydrolysis
  3. Umsetzung von Cyclopentadienylmetallcarbonylen mit Thionylhalogeniden - Neue Synthese halogenoverbrückter Cp*Co-Komplexe / Reaction of Cyclopentadienyl Metal Carbonyles with Thionylhalides - New Synthesis of Halogeno-Bridged Cp*Co Complexes
  4. Die Oxochlorovanadate PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN und (PPh4)2[VOCl4]·CH3CN mit auffälligen Abweichungen von der quadratisch-pyramidalen Anionenstruktur / The Oxochlorovanadates PPh4[VOCl3OH], PPh4[VOCl4], (PPh4 )2 [VOCl4 ]·2CH3CN and (PPh4)2[VOCl4]·CH3CN with Remarkable Deviations from the Square-Pyramidal Anion Structure
  5. S-, X-, Q- und W-Band-Pulver-EPR-Untersuchungen an Tetra-n -butylammonium-bis( 1,2-dicyanoethen-1,2-dithiolato)aurat(II), [(n-C4H9)4N]2[AuII(mnt)2] / S, X, Q and W Band Powder-EPR Investigations on Tetra-n-butylammoniumbis( 1,2-dicyanoethylene-1,2-dithiolato)aurate(II), [(n-C4H9)4N]2 [AuII(mnt)2]
  6. Unerwartete Reaktionsprodukte bei der Umsetzung von Mesitylmagnesiumbromid mit Arsentribromid / Unexpected Products from the Reaction of Mesitylmagnesium Bromide and Arsenic Tribromide
  7. 1.3.5-Triazin-2,4,6-trisulfenyltrichlorid: Synthese, Eigenschaften und Reaktionsverhalten / 1.3.5-Triazine-2,4,6-trisulfenyltrichloride: Synthesis, Properties and Reactions
  8. Verdampfungsverhalten von Lanthantrihalogeniden / Evaporation Behaviour of Lanthanum Trihalides
  9. Synthese und Molekülstruktur des [α-(Dichlormethylsilyl)ethyl]- dichlorboran-dimethylsulfid / Synthesis and Molecular Structure of [α-(Dichloromethylsilyl)ethyl]- dichloroborane-dimethylsulfide
  10. Organogallitimamide: Synthese und Kristallstrukturen von [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2 / Organogallium Amides: Synthesis and Crystal Structures of [iPr2GaN(H)tBu]2 und [Mes(Cl)GaN(H)tBu]2
  11. α-Dicarbonylmonoxime als Nucleophile und Nachbargruppen / α-Dicarbonylmonoximes as Nucleophiles and Neighbour Groups
  12. Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides
  13. A Short and Productive Synthesis of Racemic α-Lipoic Acid
  14. A Short and Productive Synthesis of (R)-α-Lipoic Acid
  15. 5,10,15,20-Tetrakis(diphenylmethyl)porphyrin - A Nonplanar Porphyrin with Intermediate Degree of Ruffling
  16. Synthesis of 3-Amino(alkoxy)-2,4-dioxo-1,3-oxazolidine-5-carboxylates from Tartronic Esters
  17. Cyanothioacetamide and its Derivatives in Heterocyclic Synthesis: A New Route for the Synthesis of Several Pyridine and Thieno[2,3-b]pyridine Derivatives and their Biological Evaluation
  18. Synthese und Struktur von Prolinring-modifizierten Actinomycinen des X-Typs / Synthesis and Structure of Proline Ring Modified Actinomycins of the X-Type
  19. Neighbouring Group Participation of C-6 Substituents of Glucose Derivatives on the Stereoselectivity of the N-Glycosidic Linkage of Glycopeptides
  20. Synthese und Kristallstruktur von 3.6-Di-tert-butylpyridazin / Synthesis and Crystal Structure of 3.6-Di-tert-butylpyridazine
  21. p-Tolyl(trimethylsilylethynyl)sulfone as Synthon for the Synthesis of Cp(OC)2M-C =CSiMe3 (M ≡ Fe, Ru). Molecular Structure of Cp(OC)2Fe-C ≡ CSiMe3
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