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

Literature Information

Publication Date 2015-12-28
DOI 10.1039/C5QO00315F
Impact Factor 5.281
Authors

A. Acharya, J. A. Eickhoff, K. Chen, V. J. Catalano, C. S. Jeffrey


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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.

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DOI: 10.1039/C4PY90044H

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Self-citation Rate: 8.7%
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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