Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(8): 1297-1300
DOI: 10.1055/s-2005-861867
DOI: 10.1055/s-2005-861867
PAPER
© Georg Thieme Verlag Stuttgart · New York
Simplistic Expedient and Practical Synthesis of (±)-α-Lipoic Acid
Further Information
Received
10 November 2004
Publication Date:
09 March 2005 (online)
Publication History
Publication Date:
09 March 2005 (online)
Abstract
Synthesis of α-lipoic acid has been achieved by a simple sequence of reactions. The synthesis highlights the use of α-chloroesters in a Reformatsky reaction. The intermediate keto acid is an intermediate from which both isomers of lipoic acid can be prepared.
Key words
Reformatsky reaction - α-chloroesters - α-lipoic acid - ozonolysis
- 1
Herbert AA.Guest JR. Arch. Microbiol. 1975, 106: 259 - 2
Reed LJ. Compr. Biochem. 1966, 14: 99 - 3
Reed LJ.Hackert ML. J. Biol. Chem. 1990, 256: 8971 - 4
Bast A.Haenen GRMM. Biochim. Biophys. Acta 1988, 963: 558 - 5
Baur A.Harrer T.Jahn G.Kalden JR.Fleckenstein B. Klin. Wochenschr. 1991, 69: 722 - 6
Muller L.Menzel H. Biochim. Biophys. Acta 1990, 1052: 386 - 7
Podda M.Tritschler HJ.Ulrich H.Packer L. Biochem. Biophys. Res. Commun. 1994, 204: 98 - 8
Marshell AW.Graul RS.Morgan MY.Sherlock S. Gut 1982, 23: 1088 - 9
Plotzker R.Jensen D.Payne JA. Am. J. Med. Sci. 1979, 283 - 10
Gandhi VM.Wagh SS.Natraj CV.Menon KKG. J. Biosci. 1985, 9: 117 - 11
Alterkrich H.Stoltenburg-Didinger G.Wagner HM.Herrmann J.Walter G. Neurotoxicol. Tetratol. 1990, 12: 619 -
12a
Brookes MH.Golding BT.Howes DA.Hudson AT. J. Chem. Soc., Chem. Commun. 1983, 1051 -
12b
Brookes MH.Golding BT.Hudson AT. J. Chem. Soc., Perkin Trans. 1 1988, 9 - 13
Rao AVR.Gurjar MK.Garyali K.Ravindranathan T. Carbohydr. Res. 1986, 148: 51 - 14
Rao AVR.Punrandare AV.Reddy ER.Gurjar MK. Synth. Commun. 1987, 17: 1095 - 15
Rao AVR.Mysorekar SV.Gurjar MK.Yadav JS. Tetrahedron Lett. 1987, 28: 2183 - 16
Rao AVR.Mysorekar SV.Yadav JS. Synth. Commun. 1987, 17: 1339 - 17
Elliott JD.Steele J.Johnson WS. Tetrahedron Lett. 1985, 26: 2535 - 18
Page PCB.Rayner CM.Sutherland IO. J. Chem. Soc., Chem. Commun. 1986, 1408 - 19
Menon RB.Kumar MA.Ravindranathan T. Tetrahedron Lett. 1987, 28: 5313 - 20
Gopalan AS.Jacobs HK. J. Chem. Soc., Perkin. Trans. 1 1990, 1897 - 21
Laxmi YRS.Iyengar DS. Synthesis 1996, 594 - 22
Rao BV.Rao AS. Synth. Commun. 1995, 25: 1531 -
23a
Adger B.Bes MT.Grogan G.McCaque R.Pedragosa MS.Roberts SM.Villa R.Wan PWH.Willetts A. J. Bioorg. Med. Chem. 1997, 5: 253 -
23b
Chavan SP.Praveen C.Ramakrishna G.Kalkote UR. Tetrahedron Lett. 2004, 45: 6027 ; and the references cited therein - 24
Chavan SP.Shivasankar K.Sivappa R. J. Chem. Res. 2004, 406 - 25
Rieke RD.Uhm SJ. Synthesis 1975, 452 - 26
Santaniello E.Manzocchi A. Synthesis 1977, 698 - 27
Picotin G.Miginiac P. J. Org. Chem. 1987, 52: 4796 - 28
Das J.Chandrasekaran S. Tetrahedron 1994, 40: 11709 - 29
Jackson AC.Goldman BE.Snider BB. J. Org. Chem. 1984, 49: 3988 - 30
Lewis BA.Raphael RA. J. Chem. Soc. 1962, 4263