Journal of Organic Chemistry 2003-11-14

Allylation of erythromycin derivatives: introduction of allyl substituents into highly hindered alcohols.

Eric J Stoner, Matthew J Peterson, Michael S Allen, John A DeMattei, Anthony R Haight, M Robert Leanna, Subhash R Patel, Daniel J Plata, Ramiya H Premchandran, Michael Rasmussen

Index: J. Org. Chem. 68(23) , 8847-52, (2003)

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Abstract

Functionalized erythromycin 9-oxime derivatives are 6-O-allylated under mild conditions using substituted allyl tert-butyl carbonates under palladium(0) catalysis. This allylation works well where traditional ether-forming protocols function poorly. Allyl tert-butyl carbonates provide higher yields in this reaction than lesser substituted carbonates such as ethyl or isopropyl. Aryl-substituted allyl carbonates or carbamates may be employed as well and, when used, produce trans-olefinic products.