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An asymmetric aminohydroxylation approach to the azepine core of (-)-balanol
C E Masse1, A J Morgan, J S Panek
1Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering Boston University, Massachusetts 02215, USA.
Organic Letters
|September 16, 2000
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.