American Chemical Society
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An Anion-Induced Regio- and Chemoselective Acylation and Its Application to the Synthesis of an Anticancer Agent

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journal contribution
posted on 2001-10-20, 00:00 authored by Marc Poirier, Frank Chen, Charles Bernard, Yee-Shing Wong, George G. Wu
An efficient Grignard- and organolithium-induced regio- and chemoselective anionic acylation is reported. A number of tricyclic ketones are prepared in good to excellent yields via this method. This method is complementary to the Frieldel−Crafts acylation for electron-deficient substrates. A novel anisole-based Grignard reagent was developed to effect the cyclization of sterically hindered substrates. This novel reagent has been successfully applied to the synthesis of Sch 66336, a candidate for oncologic treatment.