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Synthesis of 3-substituted analogues of levulinic acid via Baylis-Hillman and Mukaiyama reactions. Potential inhibitors of Porphobilinogen Synthase.

Pavel Bobál' and Reinhard Neier*

Department of Chemistry, University of Neuchâtel, CH-2000 Neuchâtel , (Switzerland)



1. Introduction

1.1. Importance of the "pigments of life"

1.2. Relation between the biosynthetic pathway and a potential prebiotic pathway to porphobilinogen

1.3. Mechanistic alternatives for the biosynthesis of porphobilinogen in comparison with a recent synthesis

1.4. Biochemical knowledge about the enzyme porphobilinogen synthase

1.5. Additional information about porphobilinogen synthase obtained with the help of genetic engineering

1.6. Recent inhibition studies of porphobilinogen synthase

1.7. Structure of inhibitors which could be used in biased libraries

2. Synthesis of derivatives of levulinic acid as potential analogues of postulated intermediates of the biosynthesis of porphobilinogen

2.1. Synthesis using alkylation of b-ketoesters

2.2. Synthesis using aldol reactions and Mukaiyama aldol reactions

2.3. Synthesis using the Baylis-Hillman approach

3. Conclusions

4. Experimental

5. Acknowledgements

6. References