Combination of enzymatic procedures with multicomponent condensations
R. Ostaszewski, D. E. Portlock, A. Fryszkowska, and K. Jeziorska
1Institute of Organic Chemistry PAS, 01-224 Warsaw,
Kasprzaka 44/52, Poland; 2Faculty of Chemistry, Warsaw University of
Technology, 00-664 Warsaw, Noakowskiego 3, Poland; 3Combinatorial Chemistry
Section, Procter & Gamble Pharmaceuticals, Health Care Research
Center, 8700 Mason Montgomery Road, Mason, OH 45040, USA
Abstract: A new synthetic method based on combination
of enzymatic desymmetrization of 3-phenylglutaric anhydrides with multicomponent
condensation is outlined. Enzymatic monoesterification of glutaric anhydrides
was performed, and the derived monoacids were used as substrates for
subsequent Ugi and Passerini multicomponent condensations. Both reactions
were combined as two-step, one-pot processes. The choice of solvent
and enzyme type has an appreciable effect on the course of reactions.
*Pure Appl.Chem. 75,
141�419 (2003). An issue of reviews and research papers based on
lectures presented at the 23rd IUPAC International Symposium on the
Chemistry of Natural Products, Florence, Italy, 28 July � 2 August 2002.
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