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Synthetic Studies on Erythromycin Derivatives: Reactivity of

By The C- Alkene and Wei-min Chen

Abstract

Abstract: The reactivity of the C12-21 alkene of some erythromycin A derivatives was studied. This double bond was easily oxidized to the corresponding epoxide with excellent stereoselectivity. A single crystal X-ray structure showed that the epoxide moiety was on the same side as the acetonide. When an erythromycin derivative containing a C12-21 alkene was treated with diazomethane a [3+2] cycloaddition affording a pyrazoline occurred. In the case of 6-O-allylated erythromycin derivatives the C12-21 alkene was selectively epoxidized in the presence of the 6-O-allyl moiety. These results show that the C12-21 alkene is an active reaction site, which can be used for useful further modification of erythromycin derivatives

Topics: Erythromycin, alkene, epoxidation, cycloaddition, pyrazoline
Year: 2013
OAI identifier: oai:CiteSeerX.psu:10.1.1.297.592
Provided by: CiteSeerX
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