Synthesis of coumestans by selective electrophilic cyclization followed by palladium-catalyzed intramolecular carbonylation: An efficient synthesis of coumestrol

ORGN 88

Dawei Yue and Richard Larock. Department of Chemistry, Iowa State University, Ames, IA 50011

 

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Coumestan and its derivatives are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of o-iodoanisole and terminal alkynes and selective electrophilic cyclization using I2, followed by palladium-catalyzed intramolecular carbonylation.  Biologically interesting coumestrol has been synthesized in 75% overall yield.

 

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004