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PubMed1983

Mass fragmentographic determination of homovanillic and 4-hydroxy-3-methoxy mandelic acids in 50 microliter plasma.

A method is presented for the mass fragmentographic determination of homovanillic and 4-hydroxy-3-methoxy mandelic acids in 50 microliter plasma or serum. The values found in normal, healthy adults agree well with previously published reports which required, however, much larger plasma volumes. The method uses a simple ethyl acetate extraction from acidified plasma and a one-step derivatisation with trifluoroethanol and pentafluoropropionic anhydride. The deuterium-labelled analogues are used as internal standards.

Adult↗
PubMed2004

Highly diastereoselective arylation of (S)-mandelic acid enolate: enantioselective synthesis of substituted (R)-3-hydroxy-3-phenyloxindoles and (R)-benzylic acids and synthesis of nitrobenzophenones.

An easy access to substituted (R)-3-hydroxy-3-phenyloxindoles, (R)-benzylic acids, and benzophenones is described. The reaction of the lithium enolate of the (2S,5S)-cis-1,3-dioxolan-4-one derived from optically active (S)-mandelic acid and pivalaldehyde with several o- and p-halonitrobenzenes proceeds readily to give the corresponding arylation products in good yields and diastereoselectivities. The reduction of the nitro group with Zn/HCl/EtOH in the o-nitro arylation products with concomitant intramolecular aminolysis of the dioxolanone moiety leads directly to enantiomerically pure (R)-3-hydroxy-3-phenyloxindoles. On the other hand the basic hydrolysis of the dioxolanone moiety in all the arylation products (ortho and para) leads to enantiomerically pure substituted (R)-benzylic acids. The oxidative decarboxylation of these latter with oxygen as terminal oxidant in the presence of pivalaldehyde and the Co(III)-Me2opba complex as catalyst gives substituted nitrobenzophenones.

Journal Article↗