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Issue 3, 2016

Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3) cyloaddition reactions of aza-oxyallylic cation intermediates

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Abstract

The intramolecular aza-(4 + 3) cycloaddition reactions of in situ generated aza-oxyallylic cations and furans have been reported for the construction of medium sized hydroxamate macrocycles. This method provides direct access to 12–18 membered bicyclic macrocycles. The highly functionalized macrocycles have been transformed easily in to a wide range of highly functionalized heterocyclic scaffolds including lactones and lactams that could serve the synthesis of complex macrocyclic natural products and pharmaceuticals.

Graphical abstract: Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3) cyloaddition reactions of aza-oxyallylic cation intermediates

Supplementary files

Article information


Submitted
13 Oct 2015
Accepted
27 Dec 2015
First published
28 Dec 2015

Org. Chem. Front., 2016,3, 330-334
Article type
Research Article
Author version available

Access to bicyclic hydroxamate macrocycles via intramolecular aza-(4 + 3) cyloaddition reactions of aza-oxyallylic cation intermediates

A. Acharya, J. A. Eickhoff, K. Chen, V. J. Catalano and C. S. Jeffrey, Org. Chem. Front., 2016, 3, 330 DOI: 10.1039/C5QO00315F

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