From N-triisopropylsilylpyrrole to an optically active C-4 substituted pyroglutamic acid: total synthesis of penmacric acid.
The stereoselective synthesis of penmacric acid, an optically active C-4 substituted pyroglutamic acid, has been efficiently achieved through an unusual 11-step sequence starting from simple N-triisopropylsilylpyrrole. The key steps are the initial addn. of the N-triisopropylsilylpyrrole onto a chiral nitrone, reductive hydrogenation of the pyrrole ring, followed by oxidn. of the corresponding pyrrolidine into pyrrolidinone to the desired pyroglutamic acid moiety. [on SciFinder(R)]
Références
- Titre
- From N-triisopropylsilylpyrrole to an optically active C-4 substituted pyroglutamic acid: total synthesis of penmacric acid.
- Type de publication
- Article de revue
- Année de publication
- 2009
- Auteurs
- Berini, Christophe, Pelloux-Leon Nadia, Minassian Frédéric, and Denis Jean-Noël
- Revue
- Org. Biomol. Chem.
- Volume
- 7
- Pagination
- 4512–4516
- ISSN
- 1477-0520
- DOI
- 10.1039/b911217k
Soumis le 12 avril 2018