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Synthesis 2009(21): 3571-3578  
DOI: 10.1055/s-0029-1216983
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Straightforward Total Synthesis of 2-O-Feruloyl-l-malate, 2-O-Sinapoyl-l-malate and 2-O-5-Hydroxyferuloyl-l-malate

Florent Allais*, Sophie Martinet, Paul-Henri Ducrot*
INRA, UMR206 Chimie Biologique, 78026 Versailles, France
Fax: +33(1)30833119; e-Mail: florent.allais@versailles.inra.fr; e-Mail: ducrot@versailles.inra.fr;
Further Information

Publication History

Received 29 May 2009
Publication Date:
03 September 2009 (online)

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Abstract

A synthetic method for the preparation of 2-O-feruloyl-l-malic acid, 2-O-sinapoyl-l-malic acid and 2-O-5-hydroxy­feruloyl-l-malic acid from malic acid and ferulic, sinapic, and hydroxyferulic­ acids, respectively, using Steglich esterification is described.

Key words

isourea - cross-coupling - esterification - phenol - total synthesis

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E/Z ratios were determined from the corresponding ¹H NMR spectra.

12

In order to remain consistent throughout the paper, all labeling positions refer to Figure  [¹] . Therefore, OCH3 is always at C-3′ regardless of IUPAC numbering rules.