Facile Synthesis of Naphthoquinone Spiroketals by Diastereoselective Oxidative [3 + 2] Cycloaddition

A highly selective oxidative [3 + 2] cycloaddition of chiral enol ethers and hydroxynaphthoquinone is described. This convergent strategy is amenable to an enantioselective synthesis of β-rubromycin and related naphthoquinone spiroketals. Several compounds were found to inhibit DNA-polymerase and te...

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Bibliographic Details
Published in:Organic letters 2007-12, Vol.9 (26), p.5537-5540
Main Authors: Wu, Kun-Liang, Wilkinson, Stephanie, Reich, Norbert O, Pettus, Thomas R. R
Format: Article
Language:English
Subjects:
Cyclization
Naphthoquinones - chemical synthesis
Oxidation-Reduction
Stereoisomerism
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Summary:A highly selective oxidative [3 + 2] cycloaddition of chiral enol ethers and hydroxynaphthoquinone is described. This convergent strategy is amenable to an enantioselective synthesis of β-rubromycin and related naphthoquinone spiroketals. Several compounds were found to inhibit DNA-polymerase and telomerase in a manner resembling α-rubromycin and β-rubromycin.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702450d