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 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.
Berini
Christophe
C
Département de Chimie Moléculaire (SERCO), UMR-5250, ICMG FR-2607, Université Joseph Fourier, CNRS, BP-53, 38041 Grenoble cedex 9, France.
Pelloux-Léon
Nadia
N
Minassian
Frédéric
F
Denis
Jean-Noël
JN
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
D000596:Amino Acids; C546214:N-triisopropylsilylpyrrole; D011758:Pyrroles; D011760:Pyrrolidinones; D012821:Silanes; C480950:penmacric acid; D011761:Pyrrolidonecarboxylic Acid