Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues.
Alkylation reactions using alpha-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.
Anwar
Muhammed
M
Department of Chemistry, Dyson Perrins Laboratory, The University of Oxford, South Parks Road, Oxford, OX1 3QY.
Bailey
Jonathan H
JH
Dickinson
Laura C
LC
Edwards
Hermia J
HJ
Goswami
Rajesh
R
Moloney
Mark G
MG
D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis*; D002625:Chemistry, Organic / Q000379:methods; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000596:Amino Acids; D007097:Imines; D011760:Pyrrolidinones; C480950:penmacric acid; D011761:Pyrrolidonecarboxylic Acid; D005998:Glycine