title: Studies toward the synthesis of (-)-zampanolide: preparation of N-acyl hemiaminal model systems.
abstract: [structure: see text] Synthesis of N-acyl hemiaminal model systems related to the side chain of the antitumor natural product zampanolide is reported. Key steps involve oxidative decarboxylation of N-acyl-alpha-amino acid intermediates, followed by ytterbium triflate mediated solvolysis. Evidence for stabilization of the N-acyl hemiaminal moiety in model compounds by an intramolecular hydrogen-bonding network is described.
authors.affiliation: Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Dawn M
authors.initials: DM
authors.lastname: Troast
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
chemical_list: D000970:Antineoplastic Agents; D018942:Macrolides; C444900:zampanolide