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.
Highlights
Erythromycin A (1, Figure 1) is one of the most successful antibiotics ever discovered, and has been used for the treatment of bacterial infections over the past 50 years
We have previously reported erythromycin derivatives with modifications at the C12-21 alkene [5]
We report the design and synthesis of new erythromycin intermediates with modifications at the C12-21 alkene
Summary
Erythromycin A (1, Figure 1) is one of the most successful antibiotics ever discovered, and has been used for the treatment of bacterial infections over the past 50 years. The C12-21 alkene is a reactive site of erythromycin A derivatives, which can be oxidized to an epoxide by organic peroxyacids, even in the presence of a 6-O-allyl moiety in the same molecule.
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