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Title: Divergent strategy for the synthesis of alpha-aryl-substituted fosmidomycin analogues
Authors: Devreux, Vincent ×
Wiesner, Jochen
Jomaa, Hassan
Rozenski, Jef
Van der Eycken, Johan
Van Calenbergh, Serge #
Issue Date: 2007
Publisher: American Chemical Society
Series Title: Journal of Organic Chemistry vol:72 issue:10 pages:3783-3789
Abstract: Fosmidomycin is the first representative of a new class of antimalarial drugs acting through inhibition of
1-deoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase (DXR), an essential enzyme in the nonmevalonate
pathway for the synthesis of isoprenoids. This work describes a divergent strategy for the
synthesis of a series of R-aryl-substituted fosmidomycin analogues, featuring a palladium-catalyzed Stille
coupling as the key step. An R-(4-cyanophenyl)fosmidomycin analogue emerged as the most potent analogue in the present series. Its antimalarial activity clearly surpasses that of the reference compound fosmidomycin.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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