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Feruloylbenzotriazole and Weinreb Amide as Bioinspired Building Blocks: A Reactivity Study towards O‐, N‐, S‐, and C‐Nucleophiles
Author(s) -
Roman Bart I.,
Monbaliu JeanChristophe,
De Coen Laurens M.,
Verhasselt Sigrid,
Schuddinck Bart,
Van Hoeylandt Evelien,
Stevens Christian V.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301895
Subject(s) - chemistry , nucleophile , amide , ferulic acid , reagent , reactivity (psychology) , biomimetic synthesis , combinatorial chemistry , molecule , organic chemistry , biochemistry , catalysis , medicine , alternative medicine , pathology
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.