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Issue 21, 2020
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Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives

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The synthesis of enantiomerically pure B-ring fluorinated catechin derivatives is presented. In a convergent approach the chromane was obtained by reaction of a lithiated fluoro-resorcine with an optically active epoxide. The latter was prepared from 3,4-difluorobenzaldehyde by reaction with vinylmagnesium bromide followed by Sharpless epoxidation. The protocol provides access to both fluorinated catechin as well as epicatechin derivatives.

Graphical abstract: Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives

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Article information

01 Apr 2020
13 May 2020
First published
19 May 2020

Org. Biomol. Chem., 2020,18, 4024-4028
Article type

Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives

D. D. S. Thieltges, K. D. Baumgarten, C. S. Michaelis and C. Czekelius, Org. Biomol. Chem., 2020, 18, 4024
DOI: 10.1039/D0OB00686F

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