Synthesis of functionalized pyrrolidin-2-ones and (S)-Vigabatrin from pyrrole.
Starting from pyrrole, the novel 3,4-didehydropyrohomoglutamate 8 or (ent)-8 can be efficiently synthesized in up to 91% ee, which can be utilized as a versatile building block toward functionalized pyrrolidin-2-ones. Moreover, (ent)-8 can be readily converted to (S)-Vigabatrin, being an irreversible inhibitor for GABA-T, which is used as adjunctive therapy in patients that suffer from epilepsy.
Gheorghe
Alexandru
A
Institut für Organische Chemie, Universität Regensburg, Universitätsstr. 31, 93053 Regensburg, Germany.
Schulte
Michael
M
Reiser
Oliver
O
D011758:Pyrroles / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis*; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D020888:Vigabatrin / Q000138:chemical synthesis*
C516079:2-methoxycarbonylmethyl-5-oxo-2,5-dihydropyrrole-1-carboxylic acid; D011758:Pyrroles; D011759:Pyrrolidines; D011760:Pyrrolidinones; D020888:Vigabatrin