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Archive for the ‘Corey-Chaykovsky’ Category

Taiwaniaquinone Synthesis

Posted by naturalproductman on January 26, 2011

John Hartwig and co-workers at the University of Illinois have published in JACS on the total synthesis of taiwaniaquinone – the five membered ring was formed from a Friedel-Crafts reaction mediated by a Lewis acid (BF3 etherate).  The Corey-Chaykovsky epoxidation was interesting because they state that the ylide formed from the sulfoxonium reagent did not work but the sulfonium reagent worked.

taiwaniaquinone

JACS paper

Posted in Cascade Reactions, Corey-Chaykovsky, Friedel-Crafts, Methodology, Named Reactions, Ring forming | Leave a Comment »

 
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