Issue 21, 2020

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

Abstract

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

Supplementary files

Article information

Article type
Communication
Submitted
01 اپریل 2020
Accepted
13 میٔ 2020
First published
19 میٔ 2020

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

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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