Diels-Alder Approaches for the Synthesis of Bridged Bicyclic Systems: Synthetic Applications of (7-hetero)norbornadienes

Author(s): Elena Moreno-Clavijo, Ana T. Carmona, Inmaculada Robina, Antonio J. Moreno-Vargas

Journal Name: Current Organic Chemistry

Volume 20 , Issue 22 , 2016


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Abstract:

Molecules containing bridged bicyclic systems, such as the (7-hetero)bicyclo[2.2.1]heptane ring system, are interesting synthetic targets because these systems are present in many molecules with biologically relevant activity. Common precursors for these sytems are the (7-hetero)nobornadienes. This review covers the different approaches used in the last ten years for the synthesis of (7-hetero)norbornadienes through Diels-Alder (D-A) cycloaddition between cyclic dienes and alkynes. The review also shows the synthetic applications of these [2.2.1]bicyclic systems as intermediates in the preparation of other relevant molecules.

Keywords: Alkyne dienophile, 7-azanorbornadiene, N-Boc-pyrrole, cyclopentadiene, furan, norbornadiene, 7-oxanorbornadiene, Diels-Alder cycloaddition.

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Article Details

VOLUME: 20
ISSUE: 22
Year: 2016
Published on: 16 August, 2016
Page: [2393 - 2420]
Pages: 28
DOI: 10.2174/1385272820666160215235737
Price: $58

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