2. Academic Validation
  3. Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-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

  • J Org Chem. 2011 Apr 15;76(8):2577-84. doi: 10.1021/jo102448n.
Andrew R Germain 1,  Daniel M Bruggemeyer,  Jianglong Zhu,  Cedric Genet,  Peter O'Brien,  John A Porco
Affiliations

Affiliation

  • 1 Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, United States.
PMID: 21401026 DOI: 10.1021/jo102448n
Abstract

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.

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