Enantioselective synthesis of citric acid analogues

• The enantioselective synthesis of (1S,2S)- and (1R,2S)- fluorocitric acid is described. Toxic fluorocitric acid formed enzymaticly from fluoroacetic acid has the 1R,2R configuration. The enzyme citrate (si)-synthase catalyzes the formation of all four isomers of fluorocitric acid.Stereoselectively labelled methyl 4,6-0-benzylidene- -2-deoxy-α-D-erythro-hexopyranosid-3-ulose is used in the synthesis of (1S,2S)-, (1S,2R)- and (1R,2S)-l-[ 2H2] citric acid.The absolute configuration of spiculisporic acid is determined as 3S,4S. A novel homoenolate anion equivalent to propanal, 3,3-ethylene-dioxypropyllithium, is synthesized and used in the enantioselective synthesis of spiculisporic acid.Lithium triethylborohydride cleaves the carbon— —fluorine bond in primary and secondary alkylfluorides. An investigation of the reduction of several organic fluorine compounds with this reagent is presented.

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NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

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