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
Revue
Org. Biomol. Chem.
Volume
7
Pagination
4512–4516
ISSN
1477-0520
Soumis le 12 avril 2018