Next Article in Journal
A Simple Synthetic Route to Methyl 3-Fluoropyridine-4-carboxylate by Nucleophilic Aromatic Substitution
Previous Article in Journal
Polymer – Supported Cobalt (II) Catalysts for the Oxidation of Alkenes
Molecules 2006, 11(1), 121-129; doi:10.3390/11010121
Article

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
View Full-Text   |   Download PDF [159 KB, uploaded 18 June 2014]   |  

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).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

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

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert