Journal of the Chemical Society. Perkin transactions I p. 9 - 12 (1988)
Update date:2022-07-30
Topics:
Brookes, Michael H.
Golding, Bernard T.
Hudson, Alan T.
(S)-Malic acid has been converted into α-(R)-and α-(S)-lipoic acid <(1a) and (1b), respectively> via (R)-and (S)-(2-phenylmethoxyethyl)oxirane <(2a) and (2b), respectively>.The (R)-oxirane (2a) was cleaved with but-3-enylmagnesium bromide (cuprate catalysis) to give (S)-1-(phenylmethoxy)oct-7-en-3-ol (4a).This was converted into methyl (S)-6,8-dihydroxyoctanoate (5a), the di-O-methanesulphonate (6a) of which was treated with sodium sulphide and sulphur in dimethylformamide to yield methyl α-(R)-lipoate (7a), that was saponified to α-(R)-lipoic acid (1a).The (S)-oxirane (2b) was similarly converted into α-(S)-lipoic acid (1b).
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