Synthesis of gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids from fragmentation of gamma- and delta-lactones.
A noncoded amino acid of cyclomarin A (1) was synthesized in a racemic fashion. The method employs a six-membered ring template to control the relative stereochemistry and introduction of the functional groups. Ultimately, Pd-catalyzed fragmentation of the lactone provided gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids. A Pd-catalyzed ring opening of a gamma-lactone is also reported.
Tarver
James E
JE
Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
Joullié
Madeleine M
MM
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D007783:Lactones / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry
D000596:Amino Acids; D007783:Lactones; D009842:Oligopeptides; C459019:cyclomarin A