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 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.
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA.
Kun-Liang
KL
Wu
Stephanie
S
Wilkinson
Norbert O
NO
Reich
Thomas R R
TR
Pettus
D003500:Cyclization; D009285:Naphthoquinones / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D009285:Naphthoquinones