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Media type:
E-Article
Title:
Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O‐, N‐, S‐, and C‐Nucleophiles
Contributor:
Roman, Bart I.;
Monbaliu, Jean‐Christophe;
De Coen, Laurens M.;
Verhasselt, Sigrid;
Schuddinck, Bart;
Van Hoeylandt, Evelien;
Stevens, Christian V.
Published:
Wiley, 2014
Published in:
European Journal of Organic Chemistry, 2014 (2014) 12, Seite 2594-2611
Description:
<jats:title>Abstract</jats:title><jats:p>A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2‐addition of a variety of O‐, N‐, S‐, and C‐nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3‐phenylpropenoyl Weinreb amides. The relevance of this “bioinspired” method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones.</jats:p>