An Efficient Synthesis of the Bicyclic Darunavir Side Chain Using Chemoenzymatic Catalysis

18 January 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Herein, we describe a chemoenzymatic synthesis of the bicyclic fragment of Darunavir. A ketoreductase was identified using metagenomic mining to catalyze a highly enantio- and diastereoselective dynamic kinetic resolution of a 𝛽-ketolactone. Subsequent lactone reduction with diisobutylaluminium hydride and phase transfer cyclization affords the bicyclic acetal fragment in 39% yield over four steps.

Keywords

darunavir
ketoreductase
biocatalysis
dynamic kinetic resolution

Supplementary materials

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Title
Supporting Information - An Efficient Synthesis of the Bicyclic Darunavir Side Chain Using Chemoenzymatic Catalysis
Description
Additional details, experimental procedures, characterization data, spectra and GC/HPLC traces supplementing the manuscript entitled "An Efficient Synthesis of the Bicyclic Darunavir Side Chain Using Chemoenzymatic Catalysis"
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