An asymmetric aminohydroxylation approach to the azepine core of (-)-balanol.
[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.
Masse
C E
CE
Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering Boston University, Massachusetts 02215, USA.
Morgan
A J
AJ
Panek
J S
JS
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*
D001381:Azepines; D004791:Enzyme Inhibitors; D062385:Hydroxybenzoates; C015405:ophiocordin; D011493:Protein Kinase C