Lipase-catalyzed resolution of 5-acetoxy-1,2-dihydroxy-1,2,3,4-tetrahydronaphthalene. Application to the synthesis of (+)-(3R,4S)-cis-4-hydroxy-6-deoxyscytalone, a metabolite isolated from Colletotrichum acutatum |
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Authors: | Daniel Jiménez-Teja |
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Institution: | Departamento de Química Orgánica, Facultad de Ciencias, UCA, Polígono Rio San Pedro s/n, 11510 Puerto Real, Cádiz, Spain |
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Abstract: | (+)-cis-4-Hydroxy-6-deoxyscytalone, a natural product bio-synthesized by Colletotrichum sp., has been prepared and its absolute configuration confirmed as 3R,4S, the key step being a kinetic racemic resolution of a cis-diol easily obtained from commercial 1,2,3,4-tetrahydronaphthalen-1,5-diol. Four lipases and different reaction conditions were tested in order to obtain the best yield and enantiomeric excess. Confirmation of absolute configuration was made by NMR using a single-derivatization low-temperature procedure and MPA as the auxiliary reagent. |
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Keywords: | 4-Hydroxy-6-deoxyscytalone Trihydroxytetralone Kinetic resolution Biocatalysis Absolute configuration Colletotrichum acutatum |
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