By the same authors

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Synthesis of the azaphilones (+)-sclerotiorin and (+)-8- O -methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

  • Andrew R. Germain
  • Daniel M. Bruggemeyer
  • Jianglong Zhu
  • Cedric Genet
  • Peter O'Brien
  • John A. Porco

Department/unit(s)

Publication details

JournalJournal of Organic Chemistry
DateE-pub ahead of print - 14 Mar 2011
DatePublished (current) - 15 Apr 2011
Issue number8
Volume76
Number of pages8
Pages (from-to)2577-2584
Early online date14/03/11
Original languageEnglish

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-i-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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