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Paper | Special issue | Vol 86, No. 2, 2012, pp.1055-1069
Published online, 21st September, 2012
DOI: 10.3987/COM-12-S(N)35
Advances in Siloxane-Based Coupling Reactions: Application of Palladium-Mediated Allyl-Aryl Coupling to the Synthesis of Pancratistatin Derivatives. The Formal Total Synthesis of (±)-7-Deoxypancratistatin

Krupa H. Shukla and Philip DeShong*

*Department of Chemistry and Biochemistry, University of Maryland, 7950 Baltimore Avenue, College Park, MD 20742, U.S.A.

Abstract

Palladium-mediated coupling of an allylic carbonate and an aryl siloxane has been applied to the formal total synthesis of 7-deoxypancratistatin and pancratistatin analogues. The key coupling reaction involved the use of a novel palladium olefin complex resulting in regio- and stereoselective arylation yielding a tetracyclic A-C ring intermediate. The observed regioselectivity of the coupling reaction was consistent with a model in which an unsymmetrical π-allyl palladium complex was formed. Coupling of a variety of substituted phenyl siloxane derivatives was achieved using the new Pd(0) system to provide access to novel pancratistatin derivatives.