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Macrocyclisation of 2-(5-(2-hydroxyethyl)furan-2-yl)acetic acid model compounds of nonactic acid

2009, Eng, Carine, Simone, Jean-Mary, Hartenbach, Akane, Loiseau, François, Neier, Reinhard

The macrocyclisation of hydroxyethylfuranyl acetic acid and of dehydrogenated model compounds of nonactic acid was investigated to develop a facile synthesis of nonactin analogues. By applying the Yamagushi macrocyclisation to our ω-hydroxyacids, we were able to isolate a mixture of di-, tri-, tetra- and pentameric macrocycles.

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Malonylation/Decarbalkoxylation of Furan Derivatives as Key Steps for the Preparation of Nonactic Acid Derivatives. Part I [1]

2007, Simone, Jean-Mary, Loiseau, François, Carcache, David, Bobal, Pavel, Jeanneret-Gris, Julie, Neier, Reinhard

A malonylation/decarbalkoxylation sequence from 2-substituted furans was investigated in view of developing a scalable synthesis of hydrophobic nonactic acid analogues.

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Malonylation/Decarbalkoxylation of Furan Derivatives as Key Steps for the Preparation of Nonactic Acid Derivatives. Part II [1]

2007, Simone, Jean-Mary, Loiseau, François, Carcache, David, Bobal, Pavel, Jeanneret-Gris, Julie, Neier, Reinhard

A malonylation/decarbalkoxylation sequence from 2-substituted furans was investigated in view of developing a scalable synthesis of hydrophobic nonactic acid analogues.

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Radical Couplings as Key Steps for the Preparation of Derivatives of Nonactic Acid

2007, Loiseau, François, Simone, Jean-Mary, Carcache, David, Bobal, Pavel, Neier, Reinhard

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.