Huang Yaodong, Zhang Jinsong, Pettus Thomas R R
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, USA.
Org Lett. 2005 Dec 22;7(26):5841-4. doi: 10.1021/ol0523749.
[reaction: see text] A short synthesis of (+/-)-brazilin is reported. This synthesis uses several interesting and underutilized transformations including a regioselective dirhodium-catalyzed aryl C-H insertion, a regioselective IBX phenol --> o-quinone oxidation, a tautomerization of an o-quinone to a p-quinone methide, and an intramolecular aryl cyclization with a p-quinone methide.
[反应：见正文] 报道了(±)-巴西苏木素的简短合成方法。该合成方法使用了几种有趣且未充分利用的转化反应，包括区域选择性铑催化的芳基C-H插入反应、区域选择性IBX（2-碘酰基苯甲酸）将苯酚氧化为邻醌的反应、邻醌到对醌甲基化物的互变异构反应以及与对醌甲基化物的分子内芳基环化反应。
