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

Molecules

关键词: Erythromycin;    alkene;    epoxidation;    cycloaddition;    pyrazoline;   

DOI  :  10.3390/11010121

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
© 2006 by MDPI (http://www.mdpi.org).