Résultat de la recherche
Malonylation/Decarbalkoxylation of Furan Derivatives as Key Steps for the Preparation of Nonactic Acid Derivatives. Part II [1]
A malonylation/decarbalkoxylation sequence from 2-substituted furans was investigated in view of developing a scalable synthesis of hydrophobic nonactic acid analogues.
A chemical synthesis of porphobilinogen imitating the pathway proposed by Shemin for the biosynthesis: comparing inhibition studies with investigations of chemical reactivity
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)]
The chemical synthesis of porphobilinogen an important intermediate of the biosynthesis of the "pigments of life"
Porphobilinogen is the second dedicated intermediate in the biosynthesis of «pigments of life». Only very few alkylpyrroles have been isolated from natural sources so far. The absence of stabilising substituents confers to porphobilinogen a high reactivity. The chemical synthesis of porphobilinogen had to take its sensitivity into account. The published synthesis of this unusual pyrrole are reviewed. The synthetic strategies used are analysed and compared with the biosynthesis.
Radical Couplings as Key Steps for the Preparation of Derivatives of Nonactic Acid
Free radical couplings from furan, as cheap starting material, were studied in view of developing a rapid strategy en route to the synthesis of derivatives of nonactin. The chain containing the alcohol function was introduced in one or two steps in 86% yield. For the introduction of the second chain with the ester function two different coupling methods were tested. Starting from the advanced intermediates obtained nonactin derivatives can be prepared by catalytic hydrogenation of the furan ring.
Synthesis of 3-substituted Analogues of Levulinic Acid via Baylis-Hillman and Mukaiyama Reactions. Potential Inhibitors of Porphobilinogen Synthase.
Malonylation/Decarbalkoxylation of Furan Derivatives as Key Steps for the Preparation of Nonactic Acid Derivatives. Part I [1]
A malonylation/decarbalkoxylation sequence from 2-substituted furans was investigated in view of developing a scalable synthesis of hydrophobic nonactic acid analogues.