Details

Autor(en) / Beteiligte

• Riehl, Paul S.
• Lim, Jesmine
• Finnigan, James D.
• Charnock, Simon J.
• Hyster, Todd K.

Titel

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

Ist Teil von

• Organic process research & development, 2022-07, Vol.26 (7), p.2096-2101

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 diisobutylaluminum hydride and phase transfer cyclization affords the bicyclic acetal fragment in 39% yield over four steps.