Model Studies for the Preparation of Oxepanes and Fused Compounds by Tandem [4+3] Cycloaddition/Ring‐Opening Metathesis/Cross Metathesis

Functionalised medium‐sized ether rings were prepared in an efficient manner by [4+3] cycloaddition followed by ring‐opening metathesis. This procedure provided medium‐sized rings, which were shown to be useful for the assembly of fused bicyclic structures present in complex natural compounds. The p...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-11, Vol.2017 (41), p.6202-6208
Main Authors: Disetti, Paolo, Piras, Linda, Moccia, Maria, Saviano, Michele, Adamo, Mauro F. A.
Format: Article
Language:English
Subjects:
Alkenes
Chemical synthesis
Cyclic ethers
Cycloaddition
Decomposition reactions
Ethers
Fused‐ring systems
Metathesis
Polycycles
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Summary:Functionalised medium‐sized ether rings were prepared in an efficient manner by [4+3] cycloaddition followed by ring‐opening metathesis. This procedure provided medium‐sized rings, which were shown to be useful for the assembly of fused bicyclic structures present in complex natural compounds. The potential of the chemistry described in this paper to be used in synthesis has been demonstrated by the preparation of functionalised large cyclic ethers and bicyclic structures. The preparation of cyclic‐ether building blocks has been achieved through [4+3] oxyallyl cycloaddition and a ring‐opening‐metathesis/cross‐metathesis process. These compounds are useful intermediates for organic synthesis with potential applications in natural product synthesis and fragment‐based drug discovery.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700994