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

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 copp...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-04, Vol.76 (8), p.2577-2584
Main Authors: Germain, Andrew R, Bruggemeyer, Daniel M, Zhu, Jianglong, Genet, Cedric, O’Brien, Peter, Porco, John A
Format: Article
Language:English
Subjects:
Benzopyrans - chemical synthesis
Biological Products - chemical synthesis
Chemistry
Copper - chemistry
Copper - metabolism
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Isoquinolines - chemical synthesis
Methylation
Models, Molecular
Molecular Structure
Organic chemistry
Oxidation-Reduction
Oxygen - chemistry
Preparations and properties
Pyridones - chemistry
Sparteine - chemistry
Stereoisomerism
Temperature
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo102448n