Enzymatic reduction of hydrophobic β,δ-diketo esters

Synthesis

Volumn , Issue 6, 2001, Pages 937-942

  Wolberg, Michael ^a   Ji, Aiguo ^a,b   Hummel, Werner ^c   Müller, Michael ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

^b SHANDONG UNIVERSITY   (China)

^c HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Asymmetric catalysis; Enzymatic reduction; Lactones; Natural products; Stereoselective synthesis

Indexed keywords

ALCOHOLS; ENZYMES; HYDROPHOBICITY; REDUCTION;

REGIOSELECTIVITY;

ESTERS;

ESTER DERIVATIVE; LACTONE; NATURAL PRODUCT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; DIASTEREOISOMER; ENANTIOMER; ENZYME ACTIVITY; HYDROPHOBICITY; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; REDUCTION; STEREOCHEMISTRY;

EID: 0035026590     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13393     Document Type: Article

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36. Procedure similar to: Gilbreath, S. G.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 6172.
37. -1 and the washed silica gel was dried at 105 °C for 24 h.
38. -1) were added trifluoroacetic acid anhydride (7 μL) and pyridine (5 μL). The vial was capped and incubated at 40 °C for 10 min.
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42. 6, one of the two enol forms is suppressed to approx. 5%.
43. c-5(anti)(average value; maximum deviation ±8%). Signals of the enol forms were ignored since it can be assumed that both diastereomers undergo enolization to a similar extent.
44. Data taken from the diastereomeric mixture, reference 28.
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48. 12c as described for the (4A,5S)-stereoisomer.