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The Synthesis of a Pyrazol Analogon of Porphobilinogen with the Help of the Mukaiyama Aldol Reaction

2003, Chaperon, André, Bertschy, Hugo, Franz-Schrumpf, Anne-Laurence, Hugelet, Bertrand, Neels, Antonia, Stoeckli-Evans, Helen, Neier, Reinhard

The synthesis of a pyrazol analogon of porphobilinogen is described. The Mukaiyama crossed aldol reaction is the key step of our approach. The retrosynthetic analysis follows the mechanism for the biosynthesis of porphobilinogen initially proposed by Shemin.

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Métadonnées seulement

A Chemical Synthesis of Porphobilinogen Imitating the Pathway Proposed by Shemin for the Biosynthesis: Comparing Inhibtion Studies with Investigations of Chemical Reality

1998, Bobal, Pavel, Chaperon, André, Neels, Antonia, Stoeckli-Evans, Helen, Neier, Reinhard

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Métadonnées seulement

The synthesis of a pyrazol analogon of porphobilinogen with the help of the Mukaiyama aldol reaction

2003, Chaperon, André, Bertschy, Hugo, Franz-schrumpf, Anne-laurence, Hugelet, Bertrand, Neels, Antonia, Stoeckli-Evans, Helen, Neier, Reinhard

The synthesis of a pyrazol analogon of porphobilinogen is described. The Mukaiyama crossed aldol reaction is the key step of our approach. The retrosynthetic anal. follows the mechanism for the biosynthesis of porphobilinogen initially proposed by Shemin. [on SciFinder(R)]

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Métadonnées seulement

A chemical synthesis of porphobilinogen imitating the pathway proposed by Shemin for the biosynthesis: comparing inhibition studies with investigations of chemical reactivity

1999, Bobal, Pavel, Chaperon, André, Neels, Antonia, Stoeckli-Evans, Helen, Neier, Reinhard

The synthesis of porphobilinogen and related compds. was reviewed with 78 refs. in this conference proceeding. Nature's pathways have been a strong motivation for synthetic chemists. Trying to imitate what has been shown or what is supposed to be a biosynthetic transformation always pursues several objectives: One evident goal is to obtain the natural product via the elegant way used in the natural process. The second not less important goal is to obtain insight into the mechanistic details of the biosynthetic pathway. Finally during the synthetic effort compds. are obtained which are potentially interesting as inhibitors of the natural process. Porphobilinogen, the second dedicated intermediate in the biosynthesis of 'pigments of life' synthesized following the mechanistic rationale proposed 30 yr ago by Shemin for the biosynthesis. Substances obtained during this synthetic effort and inhibitors esp. synthesized for our studies were tested in order to evaluate the different mechanistic proposals. This biomimetic approach allowed to guide at the same time the synthetic as well as the biosynthetic studies. [on SciFinder(R)]