title: From N-triisopropylsilylpyrrole to an optically active C-4 substituted pyroglutamic acid: total synthesis of penmacric acid.
abstract: 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 addition of the pyrrole nucleus onto a chiral nitrone and the obtention of the pyroglutamic acid moiety by reductive hydrogenation of the pyrrole followed by oxidation of the corresponding pyrrolidine into pyrrolidinone.
authors.affiliation: Département de Chimie Moléculaire (SERCO), UMR-5250, ICMG FR-2607, Université Joseph Fourier, CNRS, BP-53, 38041 Grenoble cedex 9, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Berini
authors.forename: Nadia
authors.initials: N
authors.lastname: Pelloux-Léon
authors.forename: Frédéric
authors.initials: F
authors.lastname: Minassian
authors.forename: Jean-Noël
authors.initials: JN
authors.lastname: Denis
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D055620:Optical Phenomena; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000596:Amino Acids; C546214:N-triisopropylsilylpyrrole; D011758:Pyrroles; D011760:Pyrrolidinones; D012821:Silanes; C480950:penmacric acid; D011761:Pyrrolidonecarboxylic Acid