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DOI: 10.1055/s-0037-1610915
Enantioconvergent Biocatalytic Redoxisomerization of Pyranones
Publication History
Publication Date:
17 September 2018 (online)
Significance
The Deska group reports an enantioconvergent biocatalytic redoxisomerization of racemic Achmatowicz-type pyranones to give valuable enantioenriched γ-hydroxy-δ-lactones by using commercially available alcohol dehydrogenases and ketoreductases. Key advantages of the developed methodology are (1) the use of a single enzyme with a dual catalytic role, (2) that only catalytic amounts of the cofactor nicotinamide are required, and (3) that both enantiomers of the γ-hydroxy-δ-lactones were accessible for several substrates.
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Comment
The authors developed a redox-neutral enzymatic hydrogen-borrowing process by identifying a formal unprecedented hydroxyenone isomerase activity of dehydrogenases. In addition, the authors connected the redoxisomerization with an organocatalytic benzoin condensation and their previously developed chloroperoxidase-catalyzed Achmatowicz rearrangement (Eur. J. Org. Chem. 2018, 2717) which enabled the synthesis of several natural products.
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