title: An asymmetric aminohydroxylation approach to the azepine core of (-)-balanol.
abstract: [reaction: see text]An efficient formal synthesis of the potent protein kinase C inhibitor (-)-balanol that relies on a modified asymmetric aminohydroxylation of the alpha,beta-unsaturated aryl ester (1) is reported. The aryl ester functionality and the dihydroquinyl alkaloid ligand system (DHQ)2-AQN are used to control the regio- and enantioselectivity of the process.
authors.affiliation: Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering Boston University, Massachusetts 02215, USA.
authors.forename: C E
authors.initials: CE
authors.lastname: Masse
authors.forename: A J
authors.initials: AJ
authors.lastname: Morgan
authors.forename: J S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D000586:Amination; D001381:Azepines / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D062385:Hydroxybenzoates / Q000138:chemical synthesis*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*
chemical_list: D001381:Azepines; D004791:Enzyme Inhibitors; D062385:Hydroxybenzoates; C015405:ophiocordin; D011493:Protein Kinase C