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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Biocatalytic Method for the Synthesis of the Key Linezolid Intermediate and Its Subsequent Conversion to Linezolid
Ravinder Reddy Patlolla1,2, Kethavath Anjali Priya Naik1,2, Linga Banoth1,2
1Department of Energy and Environmental Eng. Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Abstract:
A chemo-enzymatic approach to enantiopure (S)-linezolid 1 is presented. The key chiral intermediate, (R)-alcohol 4, was obtained via CRL lipase-catalyzed kinetic resolution of (RS)-4, affording an enantiopure (R)-alcohol 4 with 98.5% ees (enantiomeric excess of substrate) and an (S)-ester with 97.1% eep (enantiomeric excess of product). The key intermediate (R)-4 undergoes cyclization, followed by azide substitution, reductive acylation, and coupling with morpholine, affording enantiopure (S)-1 in ≥ 99% ee and 23% overall yield over six steps. This route offers an efficient biocatalytic strategy to access linezolid with high selectivity.
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