Simultaneous Synthesis of Both Rings of Chromenes via a Benzannulation/<i>o</i>-Quinone Methide Formation/Electrocyclization Cascade
作者:Nilanjana Majumdar、Keith A. Korthals、William D. Wulff
DOI:10.1021/ja210655g
日期:2012.1.18
A new route to the chromene ring system has been developed which involves the reaction of an α,β-unsaturated Fischer carbene complex of chromium with a propargyl ether bearing an alkenyl group on the propargylic carbon. This transformation involves a cascade of reactions that begins with a benzannulation reaction and is followed by the formation of an o-quinone methide, and finally results in the emergence
开发了一种色烯环体系的新路线,该路线涉及铬的α,β-不饱和费歇尔卡宾络合物与在炔丙碳上带有烯基的炔丙醚的反应。这种转化涉及一系列反应,从苯并环化反应开始,然后形成邻醌甲基化物,最后在电环化时产生色烯。通过使用芳基卡宾络合物,该反应被扩展以提供通路。这是色烯的首次合成,其中色烯系统的两个环均在一步中生成,并在 lapachenole 和维生素 E 的合成中得到突出体现。