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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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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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