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

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...

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Veröffentlicht in:Angewandte Chemie International Edition 1998-02, Vol.37 (3), p.358-360
Hauptverfasser: Chaperon, André R., Engeloch, Thomas M., Neier, Reinhard
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19980216)37:3<358::AID-ANIE358>3.0.CO;2-Y