[Stereoisomeric aromatic compounds XIX: Asymmetric reduction of 4(5)-oxocarboxylic acids with baker's yeast].
Asymmetric reduction of 4(5)-oxocarboxylic acids (esters) by baker's yeast and cyclization in acidic media yields optically active gamma(delta)-lactones. The evaluation of their chirality and optical purity was carried out by HPLC (HRGC) analysis of the corresponding 1,4(1,5)-diols via diastereomeric esters with (R)-Mosher acid (MTPA) and (S)-O-acyllactic acids respectively. By increasing the 4(5) alkyl side chain 4R(5R) configurated gamma(delta)-lactones with high ee-values are generated.
Gessner
M
M
Institut für Pharmazie und Lebensmittelchemie der Universität Würzburg, Bundesrepublik Deutschland.
Günther
C
C
Mosandl
A
A
D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D004952:Esters; D007651:Keto Acids / Q000378:metabolism*; D007783:Lactones / Q000378:metabolism; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000378:metabolism*; D013237:Stereoisomerism
D004952:Esters; D007651:Keto Acids; D007783:Lactones
Stereoisomere Aromastoffe XIX: Asymmetrische Reduktion von 4(5)-Oxocarbonsäuren mit Bäckerhefe.