title: Synthesis of gamma,delta-unsaturated and delta,epsilon-unsaturated alpha-amino acids from fragmentation of gamma- and delta-lactones.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: James E
authors.initials: JE
authors.lastname: Tarver
authors.forename: Madeleine M
authors.initials: MM
authors.lastname: Joullié
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D007783:Lactones / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry
chemical_list: D000596:Amino Acids; D007783:Lactones; D009842:Oligopeptides; C459019:cyclomarin A