Faculté des sciences

A Biomimetic Synthesis of a Porphobilinogen Precursor Using a Mukaiyama Aldol Reaction

Chaperon, André ; Engeloch, Thomas M. ; Neier, Reinhard

In: Angewandte Chemie (International Edition), 1998, vol. 37, no. 3, p. 358-360

Four steps suffice! A protected porphobilinogen was obtained in 25 % yield in a straightforward synthesis starting from a derivative of 5-aminolevulinate. The key was the use of a cyanide derivative instead of the azide. The synthesis imitates the mechanism proposed by Shemin for the biosynthesis of porphobilinogen. Phth = phthaloyl. Plus

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    Summary
    Four steps suffice! A protected porphobilinogen was obtained in 25 % yield in a straightforward synthesis starting from a derivative of 5-aminolevulinate. The key was the use of a cyanide derivative instead of the azide. The synthesis imitates the mechanism proposed by Shemin for the biosynthesis of porphobilinogen. Phth = phthaloyl.