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Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-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 O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.

journal of organic chemistry

Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-<i>O</i>-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization

Synthesis of the Azaphilones (+)-Sclerotiorin and (+)-8-O-Methylsclerotiorinamine Utilizing (+)-Sparteine Surrogates in Copper-Mediated Oxidative Dearomatization