Microbial Baeyer–Villiger oxidation applied to the synthesis of the N-protected (1R,5R)-Geisman–Waiss lactone

Using whole cell Baeyer–Villiger biooxidation as a key step and depending on the choice of the biocatalyst {E. coli TOP10[pQR239] or Acinetobacter TD63}, the synthesis of nearly enantiopure N-protected (1R,5R)-(−)-Geisman–Waiss lactone (92% ee) or its (1R,5S)-(−) regioisomer (98% ee) be performed.

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(1R,5R)-N-Carbobenzyloxy-2-oxa-6-azabicyclo[3.3.0]octan-3-oneC14H15NO4[α]D32=-107 (c 0.7, CHCl3)92% eeSource of chirality: Baeyer–Villiger biooxidationAbsolute configuration: (1R,5R)

(1R,5S)-N-Carbobenzyloxy-3-oxa-6-azabicyclo[3.3.0]octan-2-oneC14H15NO4[α]D32=-170 (c 0.3, CHCl3)94% eeSource of chirality: Baeyer–Villiger biooxidationAbsolute configuration: (1R,5S)