Journal
HETEROCYCLES
Volume 86, Issue 2, Pages 1055-1069Publisher
Japan Inst Heterocyclic Chemistry
DOI: 10.3987/COM-12-S(N)35
Keywords
Palladium; Siloxane; Allylic Coupling; 7-Deoxypancratistatin
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Funding
- National Institutes of Health, National Cancer Institute [CA 82169]
- University of Maryland
- National Science Foundation [CHE0615049]
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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 pi-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.
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