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Molecules 2006, 11(1), 121-129; doi:10.3390/11010121

Synthetic Studies on Erythromycin Derivatives: Reactivity of the C12-21 Alkene

Department of Medicinal Chemistry, School of Pharmacy, Jinan University, Guangzhou, 510632, P.R. China
Received: 8 January 2006 / Accepted: 23 January 2006 / Published: 31 January 2006
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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.
Keywords: Erythromycin; alkene; epoxidation; cycloaddition; pyrazoline. Erythromycin; alkene; epoxidation; cycloaddition; pyrazoline.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Chen, W.-M. Synthetic Studies on Erythromycin Derivatives: Reactivity of the C12-21 Alkene. Molecules 2006, 11, 121-129.

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