Enantioselective biocatalytic synthesis of (S)-monastrol.
The first enantioselective biocatalytic synthesis of (S)-monastrol has been developed via an unexpected and unusual enzymatic pathway as suitable route. Whereas attempts for a direct hydrolysis of racemic monastrol were not successful, formation of racemic O-butanoyl monastrol and subsequent enantioselective hydrolysis furnished O-butanoyl (S)-monastrol with 97% ee. Cleavage of the O-butanoyl moiety then gave the desired (S)-monastrol with 96% ee.
Blasco
Maria Alfaro
MA
Department of Chemistry and Pharmacy, University of Erlangen-Nuremberg, Henkestr. 42, 91054 Erlangen, Germany.
Thumann
Silvia
S
Wittmann
Jürgen
J
Giannis
Athanassios
A
Gröger
Harald
H
D055162:Biocatalysis; D002175:Candida / Q000201:enzymology; D005656:Fungal Proteins; D006868:Hydrolysis; D008049:Lipase / Q000378:metabolism; D011743:Pyrimidines / Q000096:biosynthesis*; D013237:Stereoisomerism; D013871:Thiones
D005656:Fungal Proteins; D011743:Pyrimidines; D013871:Thiones; C400223:monastrol; D008049:Lipase; C431349:lipase B, Candida antarctica