Synthesis of B-ring-fluorinated (−)-epicatechin gallate derivatives. Issue 21 (19th May 2020)

• Record Type: Journal Article
• Authors: Thieltges, David D. S.; Baumgarten, Kai D.; Michaelis, Carina S.; Czekelius, Constantin
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 21(2020)
• Page Start: 4024
• Page End: 4028
• Publication Date: 2020-05-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00686f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Electronically modified, fluorinated catechins and epicatechins are enantioselectively synthesized in a short, convergent sequence via kinetic resolution. 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.