European Journal of Organic Chemistry · 2021 · 14 citations · 30 references
EngineeringBiochemistryChemistryBiocatalysisCatalysisEnzymologyBiocatalyst DiscoveryBiocatalytic StereoselectivityCatalytic MechanismsEnzymatic CatalysisEnzyme KineticsIndustrial BiocatalysisAsymmetric BiocatalysisBiocatalytic SynthesisChiral Intermediate ProductionEnantioselective BiocatalysisEnzymatic ResolutionEnzymatic SynthesisKetoreductase CatalysisKinetic Resolution
Abstract Biocatalytic approaches have been investigated in order to isolate the enantiomers of Wieland–Miescher ketone ( 1 ) and of its alcoholic derivatives ( cis ‐ 2 and trans‐ 3 ). Specifically, two enzymes from our in‐house metagenomic collection of oxidoreductases, IS2‐SDR and Dm7α‐HSDH, catalyzed the kinetic resolution of the starting racemic ketone 1 or its complete conversion into two diastereomeric products, respectively. Moreover, the kinetic resolution of the racemic cis ‐alcohol ( 2 ) was very efficiently obtained (E≅2.000) by lipase PS catalyzed acetylation in dry acetone. All the products were isolated with ee≥95 %. Simple chemical elaborations of some of them allowed to isolate the missing enantiomers.
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Total Synthesis of Baccatin III and Taxol
Samuel J. Danishefsky, John J. Masters, Wendy B. Young et al. · Journal of the American Chemical Society · 1996 · 433 citations