Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 8, Pages 2577-2584Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo102448n
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Funding
- National Institutes of Health [GM-073855]
- Wyeth Research
- Merck Research Laboratories
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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-y-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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