Method of producing enantiomerically pure R-(+)-alpha-lipoic aci

Details Method of producing enantiomerically pure R-(+)-alpha-lipoic aci Method of producing enantiomerically pure R-(+)-alpha-lipoic aci

1987-08-07

1988-09-20

Lee, Mary C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

562503, 568 31, 568853, 568857, 549555, C07D33904

Patent

active

047727276

ABSTRACT:
A multistage method for producing R-(+)-.alpha.-lipoic acid and S-(-)-.alpha.-lipoic acid (thioctic acid) by reacting a compound of formula II ##STR1## by means of enantioselective epoxidation to the epoxy alcohol of formula III, ##STR2## reduction to 1,3-diol-dihydroxynone-8-ene of formula IV, ##STR3## reaction with a substituted sulfonic acid chloride to 1,3-disulfoxynone-8-ene of formula V, ##STR4## oxidation with ruthenium tetroxide to 6,8-disulfoxyoctanoic acid of formula VI ##STR5## and subsequent reaction with sodium sulfide/sulfur.

REFERENCES:
patent: 4705867 (1987-11-01), Giray et al.

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