Facile synthesis of naphthoquinone spiroketals by diastereoselective oxidative [3 + 2] cycloaddition |
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| Authors: | Wu Kun-Liang Wilkinson Stephanie Reich Norbert O Pettus Thomas R R |
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| Affiliation: | Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA. |
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| Abstract: | 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 beta-rubromycin and related naphthoquinone spiroketals. Several compounds were found to inhibit DNA-polymerase and telomerase in a manner resembling alpha-rubromycin and beta-rubromycin. |
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