Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-<i>O</i>-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization
2011-04-15T00:00:00Z (GMT) by
Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-<i>O</i>-methylsclerotiorinamine that possess the natural <i>R</i>-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-μ-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective <i>O</i>-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7<i>H</i>)-one core of (+)-8-<i>O</i>-methylsclerotiorinamine.