通过非对映选择性氧化[3+2]环加成反应简便合成萘醌螺缩酮
Facile synthesis of naphthoquinone spiroketals by diastereoselective oxidative [3 + 2] cycloaddition.
作者信息
Wu Kun-Liang, Wilkinson Stephanie, Reich Norbert O, Pettus Thomas R R
机构信息
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA.
出版信息
Org Lett. 2007 Dec 20;9(26):5537-40. doi: 10.1021/ol702450d. Epub 2007 Nov 29.
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.
摘要
本文描述了一种手性烯醇醚与羟基萘醌的高选择性氧化[3 + 2]环加成反应。这种汇聚式策略适用于对β-红菌素及相关萘醌螺缩酮进行对映选择性合成。发现几种化合物以类似于α-红菌素和β-红菌素的方式抑制DNA聚合酶和端粒酶。
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